Methyl 1-benzothiophene-3-carboxylate → 1-Benzothiophen-3-ylmethanol

HRID 2393486Notes

Reaction equation

HRID 2393486 reaction equation
[S:1]1[CH:5]=[C:4]([C:6](OC)=[O:7])[C:3]2[CH:10]=[CH:11][CH:12]=[CH:13][C:2]1=2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[S:1]1[CH:5]=[C:4]([CH2:6][OH:7])[C:3]2[CH:10]=[CH:11][CH:12]=[CH:13][C:2]1=2

Participants

4

Reactant 2

HCID 12514024Methyl 1-benzothiophene-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 27763421-Benzothiophen-3-ylmethanolYield 105.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

An ether solution (50 ml) of methyl benzo[b]thiophene-3-carboxylate (15 g) was added dropwise to a suspension of lithium aluminium hydride (3.5 g) in ether (100 ml) followed by reflux for 2 h. Usual work-up gave benzo[b]thiophen-3-yl methanol (13.5 g) as an oil.

Workup

  1. temperatureby reflux for 2 h

Sources & evidence

ORD record
ord-e8e4a27c8cc549c3bce2feb7b117d673
Source dataset
uspto-grants-1998_09
Patent number
US05807871

Reaction notes

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