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

HRID 46437Notes

Reaction equation

HRID 46437 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-ece5892732bc4cdca5888224c9c4bf89
Source dataset
uspto-grants-1979_11
Patent number
US04173572

Reaction notes

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