HCID 15544964, compound → HCID 9855496, compound

Participants

Reaction Conditions

Reaction Steps

Methylmagnesium chloride (7.1 ml of a 3M solution in ether, 21.3 mmol) was added slowly to a stirred solution of dimethylzinc (5.3 ml of a 2M solution in toluene, 10.6 mmol) in THF (80ml) under argon at 0° C. After 30 minutes the mixture was cooled to −78° C. and 2 (1.2 g, 9.7 mmol) in THF (45 ml) was added dropwise over 1 hour. The reaction mixture was stirred for 20 minutes and then quenched by the addition of saturated ammonium chloride solution (20 ml). The reaction mixture was allowed to warm to room temperature, diluted with 1N hydrochloric acid (100 ml) and extracted with ether (3×200 ml). The organic layer was washed with brine (200 ml), dried (MgSO4) and the solvent was removed under reduced pressure to yield 4 as a solution in toluene which was purified by column chromatography (SiO2, pentane-ether, 1:0 to 9:1 to give the cyclopentanone 4 (0.86 g, 63%). νmax(CDCl3)/cm−1 1733 (C═O).

Provenance & Evidence