Sodium Bicarbonate → HCID 11070762, compound

Participants

Reaction Steps

1.0 g of [4-[6-(allyl-methyl-amino)-hexyloxy]-2-hydroxy-phenyl]-(4-bromo-phenyl)-methanone (Ex. 35) in 9 ml of THF/ether (1:1) is added dropwise during 45 min. to 4.8 ml of (1.7M in THF) vinylmagnesium chloride solution at 0° C. The solution is left to warm to room temperature overnight, treated with 3 ml of acetic acid/water (1:1) and worked up with saturated sodium bicarbonate solution/methylene chloride. After drying the organic phase is concentrated and the residue is purified over silica gel with methylene chloride/methanol (95:5). There is obtained 0.64 g of (RS)-5-[6-(allyl-methyl-amino)-hexyloxy]-2-[1-(4-bromo-phenyl)-1-hydroxy-allyl]-phenol, MS: m/e 474 (M+H+, 1Br).

Provenance & Evidence