2-(6-Methoxy-1-benzofuran-3-yl)acetic acid → 2-(6-Methoxy-benzofuran-3-yl)ethanol

HRID 1804783Notes

Reaction equation

HRID 1804783 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]2[C:7]([CH2:10][C:11](O)=[O:12])=[CH:8][O:9][C:5]=2[CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]2[C:7]([CH2:10][CH2:11][OH:12])=[CH:8][O:9][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 7368182-(6-Methoxy-1-benzofuran-3-yl)acetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 236144442-(6-Methoxy-benzofuran-3-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (6-methoxy-benzofuran-3-yl)-acetic acid (10.16 g, 49.3 mmol) in 500 ml of THF is cooled in an ice-bath. To this solution is added LAH (1M in THF, 49.3 ml, 49.3 mmol) and stirring is continued for 1 hour. The reaction mixture is then poured onto ice cold 1N HCl and extracted 3-times with EtOAc. The combined organic layers are dried and evaporated.

Workup

  1. additionThe reaction mixture is then poured onto ice cold 1N HCl
  2. extractionextracted 3-times with EtOAc
  3. customThe combined organic layers are dried
  4. customevaporated

Sources & evidence

ORD record
ord-587f7572818a41c5ab07c5d0599b1e21
Source dataset
uspto-grants-2013_01
Patent number
US08354431B2

Reaction notes

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