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

HRID 31172Notes

Reaction equation

HRID 31172 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][C:5]2=[O:18].B.C1COCC1>C1COCC1>[C:12]1([CH:7]2[CH2:6][CH:5]([OH:18])[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([OH:1])[CH:3]=3)[O:8]2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 27345806-Hydroxyflavanone

Product 1

HCID 179786312-Phenylchroman-4,6-diol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. filtration2-Phenylchroman-4,6-diol was filtered

Sources & evidence

ORD record
ord-acd83c60bfc64225bb70af70ce735d22
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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