Sodium Chloride → HCID 12967235, compound

Participants

Reaction Steps

In nitrogen atmosphere, 1.50 ml (11.4 mmol) of diisopropylamin and 6.60 ml (10.6 mmol) of 1.6 M butyllithium hexane were added to 15 ml of THF anhydride at a room temperature, and the mixture was stirred for 30 minutes. Adding 10 ml of THF dissolving 1.48 g (5.32 mmol) of 1-(3-methoxybenzyloxy)-2,2,4,4-tetramethyl-3-pentanon (Compound [49]) at −78° C., the mixture was stirred for 2 hours. The reaction mixture was stirred for 200 minutes with increasing the temperature to a room temperature gradually. The mixture was added to saturated aqueous solution of sodium chloride and extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, then dried with magnesium sulfate anhydride and concentrated. The concentrate was applied to a silica gel column and the elution was carried out with the mixture of hexane and ethyl acetate (hexane:ethyl acetate=1:2) to obtain 1.30 g of 3-t-butyl-3-hydroxy-2-(3-methoxyphenyl)-4,4-dimethyl-2,3,4,5-tetrahydrofuran (Compound [50]). Yield 87.8%.

Provenance & Evidence