Diiodomethane → HCID 57812583, compound

Participants

Reaction Steps

A 50 mL round-bottomed flask was charged with DCM (1 mL) at −30° C. under nitrogen with stirring. 1 M of diethyl zinc in hexane (1 mL) was added dropwise to the flask followed by the addition of diiodomethane (520 mg, 2.0 mmol). A solution of 1-(2-chloro-3,6-difluorophenyl)-prop-2-en-1-ol (50 mg, 0.2 mmol) in DCM was added to the reaction mixture at −20° C. with stirring. The reaction mixture was allowed to warm to rt and stirred for an additional 1 h. The reaction mixture was quenched with sat. aq. NH4Cl solution (15 mL) and extracted with DCM (20 mL). The organic layer was washed with brine (15 mL), dried over anhydrous sodium sulfate, and filtered. The solvent was evaporated under reduced pressure to yield a yellow oil. The material was purified by silica gel chromatography using Hexane/EtOAc (80:20) as eluent to give the desired product as a colorless oil. 1H NMR (CDCl3, 400 MHz): δ=0.39-0.48 (m, 1H), 0.48-0.60 (m, 2H), 0.67-0.76 (m, 1H), 1.55-1.63 (m, 1H), 2.48 (dd, J=8.1, 3.5 Hz, 1H), 4.46 (t, J=8.6 Hz, 1H), 6.97-7.10 (m, 2H).

Provenance & Evidence