Sodium borohydride → Methyl 2-(3,4-dichlorophenyl)-4-hydroxychroman-3-carboxylate

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Reaction Steps

A solution of racemic methyl 2-(3,4-dichlorophenyl)-4-oxochroman-3-carboxylate (100 mg, 285 μmol) in THF (2.0 mL) was diluted with methanol (4.0 mL) and stirred on an ice/acetone bath. Sodium borohydride (11 mg, 285 μmol) was added and the resulting mixture was stirred for 40 min. After this time, the mixture was diluted with water and stirred while warming to rt. The resulting white solid was collected by filtration, washed with water and dried under vacuum to provide methyl 2-(3,4-dichlorophenyl)-4-hydroxychroman-3-carboxylate (90 mg). 1H NMR (400 MHz, CDCl3) δ ppm 3.49 (s, 3 H) 3.51 (m, 1 H) 5.26 (d, J=6.1 Hz, 1 H) 5.35 (d, J=2.5 Hz, 1 H) 6.94 (dd, J=8.1, 1.0 Hz, 1 H) 7.06 (td, J=7.6, 1.0 Hz, 1 H) 7.22-7.29 (m, 2 H) 7.47 (d, J=8.6 Hz, 1 H) 7.56 (d, J=1.5 Hz, 1 H) 7.58 (d, J=7.6 Hz, 1 H).

Provenance & Evidence