Chloroiodomethane → HCID 86596139, compound

Participants

Reaction Conditions

Reaction Steps

To 1,2-dichloroethane (100 mL) at 0° C. and under a dry nitrogen atmosphere was added Et2Zn (neat, 5.2 mL, 50.0 mmol) dropwise followed by chloroiodomethane (7.72 mL, 106.0 mmol) and the reaction mixture was stirred 5 min. (1R/S,6R/S)-6-(Hydroxymethyl)cyclohex-2-ene-1-carboxylate (3.67 g, 20.0 mmol) was then added and the reaction mixture was stirred 1 h at 0° C. followed by overnight stirring at room temperature. The reaction mixture was carefully quenched with water, the product extracted with ether, and dried on anhydrous sodium sulfate. The solvent was removed in vacuo and the product was purified by flash chromatography over silica gel (ethyl acetate/hexanes, 2/8) to afford the desired product (3αR/S,5αS/R,6αR/S,6βR/S)-octahydro-1H-cyclopropa[3,4]benzo[1,2-c]furan-1-one along with some of the uncyclized product ethyl(2R/S,3R/S)-3-(hydroxymethyl)bicyclo[4.1.0]heptane-2-carboxylate.

Provenance & Evidence