Benzyl Bromide → HCID 54398369, compound

Participants

Reaction Conditions

Reaction Steps

v)—A mixture of (3β,5α,20R)-3-[(1-ethoxyethyl)oxy]-4,4-dimethylpregna-8,14-dien-20-ol (19b; 0.80 g), dry toluene (56 ml), potassium t-butoxide (2.76 g), 18-crown-6 (0.48 g) and benzyl bromide (1.13 ml) was heated at 70° C. for 1 h. After cooling, the reaction mixture was poured into water and the product extracted into ethyl acetate. The combined organic phases were washed with water and with brine, dried over sodium sulfate, and concentrated under reduced pressure to give (3β,5α,20R)-3-[(1-ethoxyethyl)oxy]-4,4-dimethyl-20-(phenylmethoxy)pregna-8,14-diene (compound 20b; 1.92 g), which was used in the following step without further purification.

Provenance & Evidence