2-Acetyl-3-bromofuran → 1-(3-Bromofuran-2-yl)ethanol

HRID 1701095Notes

Reaction equation

HRID 1701095 reaction equation
[C:1]([C:4]1[O:5][CH:6]=[CH:7][C:8]=1[Br:9])(=[O:3])[CH3:2]>C(O)C>[Br:9][C:8]1[CH:7]=[CH:6][O:5][C:4]=1[CH:1]([OH:3])[CH3:2]

Participants

3

Reactant 1

HCID 113214142-Acetyl-3-bromofuran

Product 1

HCID 203483611-(3-Bromofuran-2-yl)ethanolYield 98.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Acetyl-3-bromofuran (1.6 g, 8.5 mmoles), made by the method of YA. L. Goldfarb, M. A. Marakathina and L. I. Belen'kii, Chem. of Heterocyclic Compounds, USSR, 6, 132 (1970) was dissolved in 15 ml of ethanol and NaHB4 (0.096 g, 26 mmoles) added at room temperature. After stirring for 1.5 hours, 3-bromo-2-(1-hydroxy-ethyl)-furan (1.60 g) was isolated as a yellow oil that was purified by chromatography with silica gel to yield 0.94 g (58%) of the pure product, NMR (CDCl3, δ) 7.33 (1H, d, J=2Hz), 6.4 (1H, d, J=2Hz), 5.13 (1H, q), 2.33 (1H, d), 1.57 (3H, d, J=7Hz).

Workup

  1. additionNaHB4 (0.096 g, 26 mmoles) added at room temperature

Sources & evidence

ORD record
ord-ca158e1166d54b44991380b36ee17414
Source dataset
uspto-grants-1980_03
Patent number
US04191693

Reaction notes

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