Hydrochloric Acid → HCID 46862984, compound

Participants

Reaction Steps

To a mixture of zinc chloride (25.0 mmoL) in water (15 mL) at about 10° C. was added 50% sodium hydroxide (49.0 mmoL) followed by water (5 mL). The mixture was stirred vigorously with a mechanical stirred at room temperature. To the mixture was added dimethyl(3,3-difluoro-2-oxoheptyl)phosphonate (17.0 mmoL) in tetrahydrofuran (15 mL). The mixture was stirred at room temperature for about an hour. To the mixture was added (5Z)-benzyl 7-[(1R,2R,3R)-3-benzyloxy-2-formyl-5-oxocyclopentyl]hept-5-enoate (17, R1 is phenyl, R2 and R3 are H and R7 is benzyl, 15.0 mmoL) in tetrahydrofuran (15 mL). The mixture was stirred at room temperature overnight. To the mixture was added dichloromethane (60 mL) and water (50 mL). The pH was adjusted to approximately 4 with 5 wt % hydrochloric acid. The layers were separated; the organic layer was dried over sodium sulfate, filtered through Celite® and concentrated to dryness. The residue was purified by column chromatography (40% ethyl acetate in heptanes) to yield (5Z)-benzyl 7-[(1R,2R,3R)-3-benzyloxy-2-[(E)-4,4-difluoro-3-oxooct-1-enyl]-5-oxocyclopentyl]hept-5-enoate (18, R1 is phenyl and R2, R3 are H and R7 is benzyl) as an oil (4.1 g).

Provenance & Evidence