Sodium Chloride → HCID 12967235, compound

Participants

Reaction Steps

In a nitrogen atmosphere, 1.50 ml (11.4 mmol) of diisopropylamine and 6.60 ml (10.6 mmol) of a 1.6 M butyl lithium hexane solution, were added to 15 ml of anhydrous THF at room temperature, followed by stirring for 30 minutes. To this solution, 1.48 g (5.32 mmol) of 1-(3-methoxybenzyloxy)-2,2,4,4-tetramethyl-3-pentanone (compound (4)) dissolved in 10 ml of THF, was added at −78° C., followed by stirring for 2 hours. The reaction solution was gradually heated to room temperature and stirred for 3 hours and 20 minutes. The reaction mixture was put into a saturated sodium chloride aqueous solution and extracted with ethyl acetate. The extract layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and then concentrated. The concentrated product was subjected to a silica gel column and eluted with a 1:2 mixed solvent of hexane and ethyl acetate, to obtain 1.30 g of 3-t-butyl-3-hydroxy-2-(3-methoxyphenyl)-4,4-dimethyl-2,3,4,5-tetrahydrofuran (compound (5)) in a yield of 87.8%. Melting point: 83.0–83.5° C. (colorless granular crystals, recrystallized from hexane and ethyl acetate)

Provenance & Evidence