Triethylamine → Hexahydrofuro(2,3-b)furan-3-ol

Temperature

55 °C

Dissolve sodium borohydride (35.5 g) in ethanol (400 ml) under nitrogen atmosphere. Ethyl-2-(2-ethoxytetrahydrofuran-3-yl)-2-oxoacetate (100 g) was dissolved in Ethanol (100 ml) and slowly added at 15-30° C. Reaction mass was then maintained at 50-60° C. for 8 hrs. Reaction mass was cooled to 20-30° C. and slowly added ammonium chloride solution (57.5 g in 100 ml water) and stirred for 1 hrs. Reaction mass was filtered and filtrate was distilled out under vacuum to residue. Dichloromethane (400 ml) was added to residue and cooled to −10° C. Hydrochloric acid (85 ml) was added slowly drop wise in 2 hours by maintaining temp 0 to −10° C. Reaction temp was maintained for 1 hr at 0 to −10° C. Triethyl amine (91.3 g) was added to the reaction mass at 0 to −10° C. and reaction mass was stirred for 1 hour at 0 to −10° C. Reaction mass was concentrated to residue. Residue was stripped out with Ethyl acetate (2×100 ml). Ethyl acetate (500 ml) was added to the residue and cooled to 10-15° C. Reaction mass was then filtered off and filtrate was concentrated to residue to get Hexahydrofuro[2,3-b]furan-3-ol (Yield 56 g).

1. additionslowly added at 15-30° C
2. customReaction mass
3. customReaction mass
4. temperaturewas cooled to 20-30° C.
5. customReaction mass
6. filtrationwas filtered
7. distillationfiltrate was distilled out under vacuum to residue
8. additionDichloromethane (400 ml) was added to residue
9. temperaturecooled to −10° C
10. additionHydrochloric acid (85 ml) was added slowly drop wise in 2 hours
11. temperatureby maintaining temp 0 to −10° C
12. customReaction temp
13. temperaturewas maintained for 1 hr at 0 to −10° C
14. customreaction mass
15. customReaction mass
16. concentrationwas concentrated to residue
17. additionEthyl acetate (500 ml) was added to the residue
18. temperaturecooled to 10-15° C
19. customReaction mass
20. filtrationwas then filtered off
21. concentrationfiltrate was concentrated to residue

ORD record

ord-ab522e8fb3164449ba295295a0afebbb

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841467B2