Mesityl oxide → HCID 86744883, compound

Participants

Reaction Conditions

Reaction Steps

2 ml of hexamethylphosphoramide was added to a solution of 1.7 g (16 millimole) of potassium t-butoxide in 15 ml of tetrahydrofuran, and cooled to -70° C. under nitrogen. 2 g (15 millimole) of the product of Step A in 4 ml tetrahydrofuran was added over the course of 5 minutes, with stirring. The stirring of the deep orange solution was continued for another 15 minutes and then a solution of 3.5 g (15 millimole) of the tosylate of cis-2-pentene-1-ol in 2 ml tetrahydrofuran was added. After 30 minutes the mixture was warmed to 0° C., maintained at that temperature for 1 hour, and then warmed to room temperature, followed by the addition of 10 ml of 1N NH4Cl. Following extraction with ether, 2.5 g of a crude, yellow-brown oil was obtained. Flash column chromatography yielded 1.1 g (16% yield) of 3-chloro-3-(cis-2-pentenyl)- 4-methyl-4-pentene-2-one: ##STR9##

Provenance & Evidence