Aluminium lithium hydride → 2-(4-Bromobenzyl)-2-[4-(diethoxymethyl)benzyl]-1,3-propanediol

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Reaction Steps

To a solution Dimethyl 2-(4-bromobenzyl)-2-[4-(diethoxymethyl) benzyl]malonate(crude from Step 2) in 200 mL of THF cooled at 0° C. was added of LiAlH4 (0.8 g). The mixture was stirred for 2 h at room temperature and the quenched with acetone (5 mL), followed by 100 mL of 20% aqueous sodium potassium tartrate solution. The mixture was extracted with 200 ML of 2:1 hexane/EtOAc. The extract was dried over Na2SO4 and concentrated to give the crude product which was purified by silica gel chromatography eluted with 2:1 hexane EtOAc containing 1% of Et3N to give 4.2 g of the title compound.

Provenance & Evidence