Ammonium Chloride → (3R,3aS,6aR)-hexahydrofuro(2,3-b)furan-3-ol

Participants

Reaction Steps

Into a mixed solution of methanol (25 ml) and 2-propanol (25 ml) was suspended (3aR, 6aR)-tetrahydrofuro[2,3-b]furan-3(2H)-one (10 g, 78.1 mmol), and sodium boron hydride (0.89 g, 23.4 mmol) was added divisionally to this at 0° C. and the mixture was stirred for 1.5 hours. After completion of the reaction, methanol (15 ml) and ammonium chloride (1.17 g, 21.9 mmol) were added and the mixture was stirred, then, the solvent was distilled off. To the concentrated residue was added 2-propanol (40 ml) and the mixture was concentrated again, and 2-propanol (40 ml) was added to this to cause dissolution. Insoluble materials were filtrated, then, concentration was performed to obtain a title compound in the form of yellow oil (9.87 g, yield 97.2%, (3R,3aS,6aR)-hexahydrofuro[2,3,b]furan-3-ol/(3S,3aS,6aR)-hexahydrofuro[2,3,b]furan-3-ol ratio=97.9/2.1).

Provenance & Evidence