Borane;tetrahydrofuran → 2-Phenylchroman-4,6-diol

Participants

Reaction Steps

Into a suspension of 6-hydroxyflavanone (1.0 g) in dry THF (11.5 ml) was added dropwise a solution of borane-THF complex (12.5 ml, 1.0 M in THF) under nitrogen. The reaction mixture was refluxed for 1 hour. After cooling to the room temperature it was poured into an ice-2 M HCl-solution. 2-Phenylchroman-4,6-diol was filtered. 1H NMR (400 MHz, d6-DMSO) δ: 8.83 (s, 1H), 7.45-7.38 (m, 4H), 7.35 (m, 1H), 6.89 (d, 1H, J 2.8 Hz), 6.59 (d, 1H, J 8.7 Hz), 6.54 (dd, 1H, J 8.7, 2.8 Hz), 5.41 (d, 1H, J 7.0 Hz), 5.11 (dd, 1H, J 11.7, 1.2 Hz), 4.87 (m, 1H), 2.26 (m, 1H), 1.90 (m, 1H).

Provenance & Evidence