Diiodomethane → 1-Phenyl-1-methylcyclopropane

Participants

Reaction Conditions

Reaction Steps

To a solution of ZnEt2 (165 mL, 169 mmol) in DCM (160 mL) at 0° C. was added a solution of TFA (6.5 mL, 85 mmol) in DCM (80 mL) dropwise and the mixture was stirred at 0° C. for 30 min. Then to above mixture was added CH2I2 (6.6 mL, 85 mmol) in DCM (80 mL) dropwise and the mixture was stirred at 0° C. for 20 min, followed by adding dropwise a solution of prop-1-en-2-ylbenzene (5.0 g, 42.3 mmol) in DCM (80 mL). The mixture was stirred at rt for 30 min, quenched by brine (100 mL), extracted with DCM (2×100 mL) and the combined organic layers were dried over Na2SO4, filtered, concentrated and purified by CC (PE/EA=1/0 to 100/1) to afford compound P43a (3.4 g, 60%) as a yellow oil.

Provenance & Evidence