Sodium Hydroxide → HCID 12146360, compound

Participants

Reaction Conditions

Reaction Steps

(2S)-4-(1-hydroxy-2-naphthyl)-1,2-butanediol (3.50 g, 15.1 mmol) was dissolved in hydrogen bromide (30 wt. % in acetic acid, 100 mL) and the reaction mixture was stirred at 0° C. for 2 h. The reaction mixture was quenched by the addition of water (500 mL) and extracted with ethyl acetate (3×200 mL). The combined organic extracts were washed with water (3×200 mL), aqueous sodium chloride (300 mL), dried (magnesium sulfate), and the solvent was removed in vacuo to provide a crude oil. The residue was dissolved in methanol (100 mL) and the resulting solution was slowly added to a solution of aqueous sodium hydroxide (2.5 M, 150 mL) in water (350 mL) and the reaction mixture was allowed to stir at 0° C. for 30 min. The reaction mixture was quenched by the addition of aqueous hydrogen chloride (1.0 M, 500 mL) and extracted with ethyl acetate (3×200 mL). The combined organic extracts were washed with water (2×200 mL), aqueous sodium chloride (300 mL), dried (magnesium sulfate), and the solvent was removed in vacuo to provide a crude oil. Purification by flash column chromatography (silica, ethyl acetate:hexanes 1:1) gave 5.38 g (70%, 50% ee) of (2R)-3,4-dihydro-2H-benzo[h]chromen-2-ylmethanol as a colorless oil. [α]D25=−51.23 (c 11.58 in chloroform, 50% ee); Rf=0.52 (silica, ethyl acetate:hexanes 1:1); Anal. Calcd. for C14H14O2.0.25 H2O: C, 76.86; H, 6.68. Found: C, 76.47; H, 6.38.

Provenance & Evidence