Sodium hydride → HCID 12967234, compound

Participants

Reaction Steps

In nitrogen atmosphere, adding dropwise 15 ml of DMF dissolving 7.05 g (44.1 mmol) of 2,2,4,4-tetramethyl-1,3-pentandiol (Compound [2]) to 80 ml of DMF suspended with 2.12 g (53.0 mmol) of 60% sodium hydride over 30 minutes, then the mixture was stirred for 30 minutes. After adding dropwise 15 ml of DMF dissolving 9.07 g (57.9 mmol) of 3-methoxybenzylchoride (Compound [47]) to the mixture over 30 minutes, the mixture was stirred for 12 hours. The reaction mixture was added to saturated aqueous solution of ammonium 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=10:1) to obtain 10.7 g of 1-(3-methoxybenzyloxy)-2,2,4,4-tetramethyl-3-pentanol (Compound [48]) as a colorless oil. Yield 86.7%.

Provenance & Evidence