Oxygen → 2-(Benzofuran-3-yl)ethanol

HRID 1095543Notes

Reaction equation

HRID 1095543 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].O=O.C[O:10][C:11](=O)[CH2:12][C:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][CH:14]=1.[H-]>C(OCC)C.O>[O:15]1[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:13]([CH2:12][CH2:11][OH:10])=[CH:14]1

Participants

7

Reactant 4

HCID 977OxygenHCID 166653HydrideHCID 10976279Methyl Benzofuran-3-acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 109538362-(Benzofuran-3-yl)ethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Procedure

LiAlH4 (1.025 g, 37.95 mmol) was suspended in diethyl ether with exclusion of oxygen. A solution of the benzofuran-3-ylacetic acid methyl ester just prepared (2.546 g, 13.4 mmol) in diethyl ether (15 ml) was then slowly added to the mixture and the mixture was stirred at room temperature for 30 min. The course of the reaction was monitored by TLC. For complete hydrolysis of the excess hydride, a mixture of water (2 ml) and diethyl ether (5 ml) was cautiously added dropwise to the mixture. The ethereal solution obtained was filtered over kieselguhr and the filter cake was rinsed with diethyl ether. After removal of the solvent, the desired alcohol was obtained in a yield of 1.93 g (89%) as a pale yellow oil and was employed for the further synthesis without further purification.

Workup

  1. additionwas then slowly added to the mixture
  2. additionwas cautiously added dropwise to the mixture
  3. customThe ethereal solution obtained
  4. filtrationwas filtered over kieselguhr
  5. washthe filter cake was rinsed with diethyl ether
  6. customAfter removal of the solvent

Sources & evidence

ORD record
ord-f096f68e76f246dabfdad7a026391d82
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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