1-Butyne, 3-(1-ethoxyethoxy)-3-methyl- → HCID 54510284, compound

Participants

Reaction Steps

A stirred solution, cooled to 9° C., of 46.8 g (0.3 mol) of 3-(1-ethoxyethoxy)-3-methyl-but-1-yne in 1.0 liters of dioxane was treated dropwise under argon with 150 ml (0.3 mol) of 2M n-butyl lithium in hexane. The solution was stirred at 7°-9° C. for 2 hours and at room temperature for 2 hours. Thereafter, there was added to the mixture a solution of 67.0 g of (20S)-1α,3β-bis(1-ethoxyethoxy)-20-methyl-21-(p-toluenesulphonyloxy)-pregn-5-ene in 0.4 liters of dioxane and, while stirring, solvent was distilled off until the internal temperature was 93° C. The mixture was then stirred at 100° C. under argon for 64 hours. After cooling, carbon dioxide was conducted into the mixture. The mixture was poured into ice water, and the emulsion was extracted with ether. The extracts were washed with saturated sodium chloride solution, dried and evaporated. There were obtained 73.6 g of crude 1α,3β,25-tris(1-ethoxyethoxy)-cholest-5-en-23-yne.

Provenance & Evidence