With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.124391-75-9,(S)-(Tetrahydrofuran-3-yl)methanol,as a common compound, the synthetic route is as follows.
A suspension of magnesium bromide (2 eq/mole, 108.17 g) in acetonitrile (300 ml) is added, at 0C, with acetic anhydride (4 eq/mole, 119.95 g). The mixture is left under stirring for 15 minutes at 0C, then 3-hydroxymethyl tetrahydrofuran (30 g, 293 mmoles) is added. The mixture is kept at the reflux temperature until complete disappearance of the substrate (18 h), then is added with 300 ml of a sodium bicarbonate saturated solution and left under stirring at room temperature for 30 minutes. The mixture is extracted with ethyl acetate (3×100 ml), the organic phase is dried over anhydrous sodium sulfate, filtered and the solvent is evaporated off to a residue. The reaction conversion is quantitative. 59.02 g (yield: 75%) of a colourless oil are obtained. The gas-chromatographic and nuclear magnetic resonance analysis of the residue show the presence of a mixture consisting of 2-acetoxymethyl-4-bromo-butyl-1-acetate and its 2-bromomethyl-4-acetoxybutyl-1-acetate isomer in a yield of 90% (53.12 g) and 10% (5.902 g), respectively. This mixture can be used directly in the subsequent reaction for the alkylation of 2-aminochloropurine (IV) as no addition products due to the presence of the minor isomer are formed. (The two isomers can anyway be separated, if necessary, by fractional distillation).2-Acetoxymethyl-4-bromo-butyl-1-acetate:1H-NMR (d, ppm): 1.83 (q, 2H, CH2) 1.98 (s, 6H, 2(CH3)) 2.07-2.13 (m, 1H, CH) 3.45 (t, 2H, CH2Br) 4.04 (d, 4H, 2(CH2O)).13C-NMR (d, ppm): 21.33 (CH2Br) 31.03(2(CH3)) 32.01 (CH2) 36.55 (CH) 64.00 (2(CH20)) 171.37 (2(CO)).2-Bromomethyl-4-acetoxy-butyl-1-acetate:1H-NMR (d, ppm): 1.63 (m, 2H, CH2) 1.88 (s, 3H, CH3) 1.90 (s, 3H, CH3) 1.99 (m, 1H, CH) 3.37 (d, 2H, CH2Br) 4.01 (d, 2H, CH2O) 4.13 (t, 2H, CH2O).13C-NMR (d, ppm): 20.55 (CH3) 21.03 (CH3) 28.37 (CH) 34.49 (CH2Br) 36.03 (CH2) 61.25 (OCH2) 66.26 (OCH2) 170.39 (CO) 170.42 (CO).
124391-75-9, 124391-75-9 (S)-(Tetrahydrofuran-3-yl)methanol 40784875, aTetrahydrofurans compound, is more and more widely used in various fields.
Reference£º
Patent; RECORDATI S.A.; WO2004/7418; (2004); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem