Chloroiodomethane → HCID 66789942, compound

Participants

Reaction Conditions

Reaction Steps

Chloroiodomethane (6.3 g, 35.5 mmol) was added to a 0° C. mixture containing 2.4 g (11.1 mmol) of methyl trans-4-methylene-2-phenylcyclopentanecarboxylate (J. Am. Chem. Soc. 1983, 105, 2315) in 25 mL of DCE followed by the addition of 17.8 mL (17.8 mmol) of Et2Zn (1M in hexanes). The reaction was stirred at 0° C. for 1 h before it was quenched with 1N HCl. The mixture was extracted with DCM (three times) and the combined extracts were dried over MgSO4 and concentrated. Column chromatography (9:1 Hexanes/EtOAc) afforded the desired compound as a colorless liquid.

Provenance & Evidence