Methanol → HCID 57166467, compound

Participants

Reaction Conditions

Reaction Steps

1 ml of dry ether was added to 141 mg of copper (I) iodide in a stream of nitrogen gas, and 1.35 ml of ether solution (1.1M) of a methyllithium was added dropwise to the mixture while cooling it by ice. The mixture was cooled down to -78° C. To the reaction mixture was added a solution of (1S, 2R)-2-chloroformyl-1-methoxycarbonylcyclohex-4-ene (50 mg) prepared by a method similar to that of Example 1 in ether (0.5 ml) at -70° C., and the mixture was stirred for one hour. After addition of methanol, the mixture was allowed to stand to return to room temperature, a saturated ammonium chloride solution was then added, and the mixture was stirred for 30 minutes. The reaction mixture was extracted with ether, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=15:85) to be purified, and thus 35 mg of the titled compound was obtained.

Provenance & Evidence