The Absolute Best Science Experiment for Ethyl tetrahydrofuran-2-carboxylate

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TETRAHYDROFURAN DERIVATIVES AS FRAGRANCES

What is proposed are specific tetrahydrofuran derivatives of the formula (I), fragrance and aroma substance mixtures comprising these tetrahydrofuran derivatives, their use in fragrance or aroma substance (mixture) and corresponding perfumed products.

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Tetrahydrofuran – Wikipedia,
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NOVEL CARBOXAMIDE DERIVATIVES AS HIV INHIBITORS

The present invention relates to carboxamide derivatives of Formula (I), where B1, B2, X, L, n, R, R1, R2, Z1, Z2, Rx and Ry are as defined in the claims, as compounds and compositions for inhibiting Human Immunodeficiency Virus (HIV) and process for making the compounds.

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Effects of trifluoroethanol as a co-solvent on the electrochemical oxidation of hardly oxidizable organic compounds

2,2,2-Trifluoroethanol was found to be a suitable co-solvent for the electrochemical oxidation of organic compounds such as cyclic ethers, gamma-butyrolactone derivatives, primary alcohols, and toluenes substituted with electron-withdrawing groups, all of which were resistant toward oxidation in methanol. The oxidation products could be utilized as worthwhile synthetic intermediates.

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Tetrahydrofuran – Wikipedia,
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Regioselective cleavage of tetrahydrofurans bearing proximate functional groups with acid iodides

Tetrahydrofurans functionalized at the C2 or C3 position (alcohols, esters, amine, ether, acetal) are cleaved with RCOCl/NaI (R = Me, tBu) in acetonitrile to give regioselectively trifunctionalized derivatives. In all cases the cleavage occurs mainly or exclusively at the C-O bond the most remote from the functional group.

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Tetrahydrofuran – Wikipedia,
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16874-34-3, Ethyl tetrahydrofuran-2-carboxylate is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 229 – Preparation of Intermediate 56 The synthesis of Intermediate 56 followed the procedure of General Procedure 2 following: Intermediate 55 Intermediate 56 To a cooled (0C) solution of ethyl tetrahydrofuran-2-carboxylate (Intermediate 55, 6 g, 41.66 mmol in THF (100 mL), dry acetonitrile (3.4 mL, 83.33 mmol) was added. After 10 min, LHDMS (1M in THF, 13.9 g, 83.3 mmol) was added. After stirring at 0C for 2 hours, the mixture was quenched with saturated citric acid solution until pH=5 and extracted into Ethyl acetate (3 x 200 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure to give 3-oxo-3-(tetrahydrofuran-2-yl)propanenitrile (Intermediate 56, 7.5 g, yield: 99%) as an oily residue that was used without further purification into the next step. m/z 140.02 [M+H]+; TLC System: 10% Methanol- dichloromethane; Rf-0.4., 16874-34-3

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Reference£º
Patent; VERSEON CORPORATION; SHORT, Kevin Michael; ESTIARTE-MARTINEZ, Maria de los Angeles; KITA, David Ben; SHIAU, Timothy Philip; (340 pag.)WO2016/138532; (2016); A1;,
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Some tips on 16874-34-3

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16874-34-3, Ethyl tetrahydrofuran-2-carboxylate is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A flask was charged with 13.6 g of magnesium and 300 ml of tetrahydrofuran, to which 60.3 g of 1,4-dibromobutane was added dropwise at 50 C. After the completion of dropwise addition, the solution was stirred at 60 C. for one hour.To the solution below 40 C., 31.0 g of ethyl tetrahydrofurancarboxylate was added dropwise.The solution was stirred at room temperature for one hour, after which an aqueous solution of ammonium chloride was added for hydrolysis.Ordinary post-treatment yielded 30.2 g of 1-(2-tetrahydrofuranyl)cyclopentanol. In 80 ml of toluene were dissolved 16.8 g of 1-(2-tetrahydrofuranyl)cyclopentanol, 13.1 g of triethylamine, and 0.5 g of 4-(N,N-dimethylamino)pyridine. Then 10.7 g of acrylic chloride was added to the solution at 50 C., which was stirred at the temperature for one hour. Water, 50 ml, was added to the solution below 30 C., followed by ordinary post-treatment. Vacuum distillation yielded 18.1 g of 1-(2-tetrahydrofuranyl)cyclopentyl acrylate. The two-step yield was 80%. [0583] boiling point: 84-86 C./86 Pa [0584] IR (thin film): nu=2954, 2871, 1720, 1635, 1619, 1450, 1402, 1298, 1207, 1170, 1074, 1049, 983, 811 cm-1 [0585] 1H-NMR (300 MHz in CDCl3): delta=1.49-2.25 (12H, m), 3.70-3.92 (2H, m), 4.57 (1H, t), 5.72 (1H, dd), 6.04 (1H, dd), 6.29 (1H, dd) ppm, 16874-34-3

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Reference£º
Patent; Hasegawa, Koji; Kinsho, Takeshi; Watanabe, Takeru; US2004/68124; (2004); A1;,
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To a solution of ethyl TETRAHYDROFURAN-2-CARBOXYLATE (Preparation 32) (1. 0965 g, 7. 604 MMOL) in anhydrous tetrahydrofuran (7 mL) AT-50 C, under an atmosphere of nitrogen, was added sodium bis (trimethylsilyl) amide (7. 6 mL of a 1. 0M solution in tetrahydrofuran, 7. 604 MMOL) dropwise. The reaction mixture was stirred for 1 hour and then a solution of 5-(tert-butyl-diphenyl-silanyloxy)-2-iodomethyl-pyridine (Preparation 31) (0. 72 G, 1. 5208 MMOL) in anhydrous tetrahydrofuran (7 mL) was added dropwise. The resulting solution was stirred at -50 C for 2 hours and then quenched with saturated aqueous ammonium chloride (25 mL). This was then extracted with ethyl acetate (3X25 mL), dried (anhydrous magnesium sulfate), filtered and concentrated in vacuo to afford the crude product. The residue was purified by flash column chromatography (hexanes to 40% ethyl acetate/hexanes) to yield a colorless oil (0. 2438 g, 33%). LRMS (m/z) : 490 (M+H) +. ‘H NMR (CDCI3, 300 MHz) 8. 07 (1 H, d, J= 2. 5 Hz), 7. 67-7. 63 (4H, m), 7. 41-7. 31 (6H, m), 6. 97 (1 H, d, J = 8. 5 HZ), 6. 86 (1 H, dd, J = 2. 8, 8. 5 HZ), 4. 21 (2H, q, J = 7. 2 Hz), 4. 09 (2H, q, J= 7. 2 HZ), 3. 22 (1 H, D, J = 13. 9 Hz), 3. 07 (1H, d, J= 13. 9 Hz), 2. 53-2. 44 (1 H, M), 2. 31-2. 15 (1 H, M), 1. 82-1. 72 (1H, m), 1. 60-1. 46 (1H, m), 1. 25 (3H, t, J = 7. 2 Hz), 1. 09 (9H, s)., 16874-34-3

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Reference£º
Patent; PFIZER INC.; WO2004/92145; (2004); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

Downstream synthetic route of 16874-34-3

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Step 2: Synthesis of ethyl 2-ethyltetrahydrofuran-2-carboxylate:A stirred solution of Diisopropylamine (about 6.5 ml) in dry THF (25 ml) was cooled to about -10 C and to this n-butyl lithium (23 ml) was added drop wise under nitrogen atmosphere and maintain the same temperature for about 45 minutes then cooled to the reaction mixture about – 75C for about 15 minutes then ethyl tetrahydrofuran-2-carboxylate (step 1, about 5 g in 30 ml THF) was added and stirred the reaction at same temperature for about 30 minutes. Increased the reaction temperature to about -35 C and stirred for 45 minutes then again cooled the reaction to about – 75C then ethyl iodide (5.2 ml in 20 ml THF) was added drop wise and the reaction temperature was slowly allowed t to reach room temperature and stirred the reaction mixture at room temperature for about 12 hours. Completion of the reaction was monitored by TLC, the reaction mixture was quenched with saturated ammonium chloride and extracted with ethyl acetate, the organic layer was washed with saturated NaHC03 followed by brine solution, the organic layer was dried over Na2S04 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using 3% ethyl acetate in hexane as eluent to furnish the title compound as light yellow colour liquid. NMR (300 MHz, CDC13): 1.40-1.44 (m, 3H); 1.77-1.87 (m, 6H); 1.88-1.96 (m, 4H); 4.78-4.85 (m, 2H); ES Mass: [M+l], 16874-34-3

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Reference£º
Patent; HETERO RESEARCH FOUNDATION; PARTHASARADHI REDDY, Bandi; VAMSI KRISHNA, Bandi; MANOHAR SHARMA, Vedula; RATHNAKAR REDDY, Kura; MADHANMOHAN REDDY, Musku; VL SUBRAHMANYAM, Lanka; PREM KUMAR, Mamnoor; WO2011/61590; (2011); A1;,
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