Sulfuric Acid → HCID 86640527, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 104 (3.0 g, 10.48 mmol) in THF (75 mL) and EtOH (50 mL), sodium borohydride (2.6 g, 68.1 mmol) was added at −20° C. followed by few drops of conc. H2SO4 and stirred for 3 h at −20° C. The reaction mixture was quenched with sat. NaHCO3 solution at −20° C. and allowed to reach room temperature. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in EtOAc. The organic layer was washed with water, dried over Na2SO4 and concentrated under reduced pressure to get crude compound which was purified through silica gel column chromatography, eluted with 15% EtOAc/hexanes to get 105 (2.3 g, 76%). 1H NMR (CDCl3) δ 7.26-7.37 (m, 5H), 5.76 (m, 1H), 5.25 (s, 2H), 3.80-3.60 (m, 3H), 2.48-2.38 (m, 1H), 2.22 (m, 2H), 1.38 (s, 3H), 1.18 (s, 3H).

Provenance & Evidence