HCID 67550769, compound → HCID 67550767, compound

Participants

Reaction Steps

To a solution of (2S)-4-[1-(benzyloxy)-2-naphthyl]-1,2-butanediol (5.63 g, 17.5 mmol) in ethanol (150 mL), palladium on carbon (10 wt. %, 0.56 g) was added, and the reaction mixture was shaken under an H2 atmosphere (50 psi) for 6 h. The reaction mixture was filtered (celite) and the solvent removed in vacuo to provide a crude oil. Purification by flash column chromatography (silica, ethyl acetate:hexanes 4:1) gave 3.81 g (94%, 50% ee) of (2S)-4-(1-hydroxy-2-naphthyl)-1,2-butanediol as a colorless oil which crystallizes upon standing. [α]D25=+11.93 (c 10.06 in chloroform, 50% ee); Rf=0.50 (silica, ethyl acetate:hexanes 4:1); mp 105-108° C.; Anal. Calcd. for C14H16O3: C, 72.39; H, 6.94. Found: C, 72.20; H, 7.18.

Provenance & Evidence