Sodium hydride → HCID 12967234, compound

Participants

Reaction Steps

In a nitrogen atmosphere, to a solution having 2.12 g (53.0 mmol) of 60% sodium hydride suspended in 80 ml of DMF at 0° C., 7.05 g (44.1 mmol) of 2,2,4,4-tetramethyl-1,3-pentanediol (compound (2)) dissolved in 15 ml of DMF, was dropwise added over a period of 30 minutes, followed by further stirring for 30 minutes. To this solution, 9.07 g (57.9 mmol) of 3-methoxybenzyl chloride (compound (1)) dissolved in 15 ml of DMF was dropwise added over a period of 30 minutes, followed by stirring for 12 hours. The reaction mixture was put into an aqueous saturated ammonium chloride 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 10:1 mixed solvent of hexane and ethyl acetate, to obtain 10.7 g of 1-(3-methoxybenzyloxy)-2,2,4,4-tetramethyl-3-pentanol (compound (3)) in a yield of 86.7% as a colorless oily substance.

Provenance & Evidence