反应详情

To a solution of dimethyl(3,3-difluoro-2-oxoheptyl)phosphonate (6.9 g, 26.5 mmoL) in MTBE (30 mL) was added LiOH.H2O (1.11 g, 26.5 mmoL) and the mixture was stirred under nitrogen for 1 h. A solution of (3aR,4R,5R,6aS)-hexahydro-2-oxo-5-(phenylmethoxy)-2H-cyclopenta[b]furan-4-carboxaldehyde (6, R1 is phenyl, and R2 and R3 are H, 6 g, 23.1 mmoL) in dichloromethane (30 mL) was added followed by NH4Cl (370 mg, 6.93 mmoL), 0.2 mL water and then the mixture was stirred for 12 h. After completion of the reaction, the reaction was then quenched with a saturated NH4Cl solution (12 mL). The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated to dryness under vacuum. The crude material was further purified by column chromatography [25% ethyl acetate in heptanes] to yield (3aR,4R,5R,6aS)-4-((E)-4,4-difluoro-3-oxo-1-octenyl)-2-oxo-5-(phenylmethoxy)hexahydro-2H-cyclopenta[b]furan (7, R1 is phenyl, and R2 and R3 are H) in 56% yield.

1. stirringthe mixture was stirred for 12 h
2. customAfter completion of the reaction
3. customthe reaction was then quenched with a saturated NH4Cl solution (12 mL)
4. customThe organic layer was separated
5. washwashed with brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated to dryness under vacuum
8. customThe crude material was further purified by column chromatography [25% ethyl acetate in heptanes]