Water → HCID 67155832, compound

Participants

Reaction Steps

A solution of methyl 2-(benzo[d][1,3]dioxol-5-yl)-4-oxochroman-3-carboxylate (58 mg, 178 μmol) in tetrahydrofuran (1.0 mL) was diluted with methanol (2.0 mL) and stirred on an ice/acetone bath. Sodium borohydride (7 mg, 178 μmol) was added and the resulting mixture was stirred for 40 min. After this time, water (about 10 mL) was added and the mixture was stirred while warming to rt. The resulting white solid was collected by filtration, washed with water and dried under vacuum to provide racemic methyl 2-(benzo[d][1,3]dioxol-5-yl)-4-hydroxychroman-3-carboxylate (51 mg, 87%). 1H NMR (400 MHz, CDCl3) δ ppm 2.69 (s, 1 H) 3.47 (dd, J=6.6, 2.5 Hz, 1 H) 3.51 (s, 3 H) 5.25 (d, J=5.6 Hz, 1 H) 5.31 (d, J=2.5 Hz, 1 H) 5.99 (s, 2 H) 6.82 (d, J=8.1 Hz, 1 H) 6.89 (d, J=8.1 Hz, 1 H) 6.92 (m, 2 H) 7.03 (t, J=7.4 Hz, 1 H) 7.23 (td, J=7.1, 1.0 Hz, 1 H) 7.57 (d, J=7.6 Hz, 1 H). Mass spectrum m/z 351.20 (M+Na)+.

Provenance & Evidence