Dimethyl Sulfoxide → 2-Isobutyl-4-pentenal

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (5.45 g, 43 mmol) was dissolved in methylene chloride (50 mL), and the solution was cooled to −78° C. Then, dimethyl sulfoxide (6.1 mL) was added dropwise thereto. To the mixture, a methylene chloride (40 mL) solution of 2-isobutylpent-4-en-1-ol (4.9 g, 34 mmol) was subsequently added dropwise, and the mixture was stirred at this temperature for 1 hour. Triethylamine (24 mL) was added thereto, and the mixture was brought to room temperature. A saturated aqueous solution of ammonium chloride was added thereto. The organic layer was separated, washed with water and saturated saline, then dried, and then concentrated to obtain the compound of interest as an oil substance. This compound was used in the next reaction without being purified.

Provenance & Evidence