Potassium Hydroxide → 5-[Decyl(dimethyl)silyl]pentanoic acid

Participants

Reaction Steps

A mixture of 6.7 g (18 mmole) of methyl-2-methoxycarbonyl-6,6-dimethyl-6-sila-n-hexadecanoate (from step C) in 50 ml of methanol and 3.0 g (about 48 mmole) of potassium hydroxide (powder) in 50 ml of methanol is refluxed for 45 min. The resulting mixture is then concentrated to a solid. Dilute hydrochloric acid (2N) is then added to the solid (in excess, to acid pH) and the mixture extracted with methylene chloride. The extract is dried, then concentrated to a residue. The residue is heated to 160°-170° under reduced pressure (approx. 15 mm Hg), for 1 hour, then distilled under high vacuum through a jacketed Vigreux column to obtain refined title product of this step (as the main fraction) at 145°-140° at 0.101-0.090 mm Hg.

Provenance & Evidence