Water → HCID 14027479, compound

Participants

Reaction Steps

4-Methyl-4-penten-1-ol (10.0 g, 0.10 mmol) is placed in 100 ml dry methylene chloride and cooled, with stirring and under nitrogen, in an acetone/dry ice bath to 0°. Triethylamine (42 ml, 0.30 mmol) is added all at once, followed by mesyl chloride (12 ml, 0.16 mmol) over a 15 min period. The mixture is stirred at 0° for 2 hr and then water is added, followed by stirring for 5 min. The mixture is worked up by extraction with water and the layers are separated. The aqueous phase is extracted with methylene chloride (2×); the organic layers are combined and washed with sat. NaHCO3, 2 N HCl, water and brine, dried over MgSO4, filtered and evaporated (not to dryness), giving 4-methyl-4-pentenyl methanesulfonate.

Provenance & Evidence