Diethyl Ether → Naphthalen-1-yl(phenyl)methanol

Participants

Reaction Steps

A solution of crude 17 (˜5 mmol, 1.0 equiv) in THF (25 mL) was cooled in an ice-bath and 3M MeMgBr in Et2O (4.0 mL, 12.0 mmol, 2.4 equiv) was added dropwise via syringe and <5° C. The mixture was stirred at <5° C. for 10 min then allowed to warm to room temperature and stirred 1 hr. The mixture was recooled to ˜8° C. and quenched with saturated NH4Cl solution (5 mL). The mixture was diluted with H2O (20 mL) and extracted with 1:1 EtOAc/heptanes (100 mL). The organic phase was washed with brine (25 mL), dried over Na2SO4, filtered and the solution concentrated under reduced pressure giving a yellow oil. The crude product was dissolved in few mL of dichloromethane/heptanes, absorbed onto silica gel and dry-loaded on a column of silica gel (30 g) packed in heptanes. The column was eluted with heptanes (150 mL), 2% EtOAc/heptanes (250 mL) and 3% EtOAc/heptanes (250 mL). Product fractions were concentrated under reduced pressure to give 1.90 g (93%) of 7 as a nearly colorless oil.

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