Hydrochloric Acid → HCID 53663024, compound

Participants

Reaction Conditions

Reaction Steps

Isopropyl cyclohexylamine (565 mg, 4 mmole) in 10 ml of anhydrous tetrahydrofuran was cooled to -78° C. in a 3 neck round bottom flask and n-butyl lithium (2 ml, 4 mmole) was added dropwise. After 10 minutes, ethyl acetate (300 mg, 4 mmole) in 5 ml of tetrahydrofuran was added dropwise over a 15 minute period and the reaction mixture was stirred for 30 minutes at -78° C. following the addition. 1,1-Diethoxy-12,15-heneicosadiene-3-one (1.5 g) in 5 ml of tetrahydrofuran was added within 1 minute and the mixture was maintained at -78° C. for another 30 minutes. 5% Aqueous hydrochloric acid (5 ml) was added and the mixture was warmed to room temperature. Solvent was removed in vacuo and 40 ml of pentane was added. The organic layer was washed until neutral and was dried, worked up to provide 1.0 g of crude reaction mixture. After purification from column chromatography, the desired product was obtained as heavy oil (1.4 g) of formula XI of Chart B.

Provenance & Evidence