Diiodomethane → HCID 57822476, compound

Participants

Reaction Conditions

Reaction Steps

A solution of diethylzinc (7.57 mL, 7.57 mmol) in dichloromethane (10 mL) was stirred at −78° C. under nitrogen as a solution of diiodomethane (1.22 mL, 15.1 mmol) in dichloromethane (10 mL) was added. The resulting mixture was stirred at −15° C. under nitrogen for 1 h to give a white milky suspension. A solution of (E)-benzyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl)carbamate (1.2 g, 3.78 mmol) in dichloromethane (10 mL) was added. The reaction mixture was stirred at rt for 1 h. and was then quenched with 1HCl. The dichloromethane layer was separated. The aqueous layer was extracted with dichloromethane (2×20 mL). The combined organic layers were washed with aqueous sodium bicarbonate (2×20 mL) and brine (20 mL), dried over magnesium sulfate, and concentrated. The residue was purified by silica gel chromatography using 0-30% EtOAc/hexane as the eluent to give benzyl ((2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropyl)methyl)carbamate as a colorless oil (0.84 g, 60%). 1H NMR (400 MHz, METHANOL-d4) d 7.42-7.22 (m, 5H), 5.07 (s, 2H), 3.12-2.84 (m, 2H), 1.20 (s, 12H), 1.17-1.12 (m, 1H), 0.71-0.60 (m, 1H), 0.58-0.44 (m, 1H), −0.28 (dt, J=9.5, 5.8 Hz, 1H). M+1=332.2.

Provenance & Evidence