With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.21461-84-7,(S)-(+)-5-Oxo-2-tetrahydrofurancarboxylic Acid,as a common compound, the synthetic route is as follows.
To a solution of 34 (1.09 g, 2.98 mmol) in dry THF (6 mL) was added a 1.5 M MeOH solution of hydrazine (6 mL). The resulting mixture was stirred at 55 C for 4 h and then poured into water and extracted with Et2O. The organic layer was washed with brine, dried (MgSO4), and concentrated to give a crude amine as a pale yellow oil. To another solution of 23 (412 mg, 3.17 mmol) and one drop of DMF in CH2Cl2 (8 mL) cooled in an ice-water bath was added slowly oxalyl chloride (0.32 mL, 3.73 mmol). The resulting mixture was stirred at rt for 2 h and then directly concentrated to give a liquid residue. This liquid was dissolved in THF (5 mL), cooled in a dry ice-acetone bath followed by the addition of Et3N (0.60 mL, 4.3 mmol) and a solution of the crude amine prepared above in THF (1 mL). The resulting mixture was stirred at rt overnight and then poured into water and extracted with CH2Cl2. The organic layer was dried (MgSO4), concentrated, and chromatographed on silica gel (hexane/EtOAc, 3:7) to give 675 mg (65%) of 36 as a yellow solid.
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Reference£º
Article; Chen, Ming-Jen; Tsai, Yeun-Min; Tetrahedron; vol. 67; 8; (2011); p. 1564 – 1574;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem