Diiodomethane → HCID 80463661, compound

Participants

Reaction Conditions

Reaction Steps

In dichloromethane (40.0 mL) was dissolved 2-methyl-1-(pyridin-3-yl)prop-2-en-1-ol (1.04 g, 6.95 mmol) obtained in Step 1. Diethylzinc (1.09 mol/L solution in n-hexane, 31.9 mL, 34.7 mmol) and diiodomethane (2.80 mL, 34.7 mmol) were added dropwise at −10° C. and the mixture was stirred at 0° C. for 2.5 hours. A saturated aqueous ammonium chloride solution and water were added to the reaction mixture. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/7) to give (1-methylcyclopropyl)(pyridin-3-yl)methanol (888 mg, 78% yield).

Provenance & Evidence