Dichloromethane → 1-(1-Benzothiophen-3-yl)ethan-1-ol

HRID 378545Notes

Reaction equation

HRID 378545 reaction equation
[S:1]1[CH:5]=[C:4]([CH2:6][C:7](OC)=O)[C:3]2[CH:11]=[CH:12][CH:13]=[CH:14][C:2]1=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(Cl)Cl.[O:24]1CCCC1>>[S:1]1[CH:5]=[C:4]([CH:6]([OH:24])[CH3:7])[C:3]2[CH:11]=[CH:12][CH:13]=[CH:14][C:2]1=2

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8028Tetrahydrofuran2×HCID 238124Methyl 2-(1-benzothiophen-3-yl)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 129927691-(1-Benzothiophen-3-yl)ethan-1-ol

Procedure

A solution of methyl benzo[b]thiophen-3-ylacetate (69 g) in dry tetrahydrofuran (100 ml) was added dropwise to a suspension of lithium aluminium hydride (10 g) in dry tetrahydrofuran (500 ml) at room temperature followed by reflux for 1 h. Hydrolysis with water, filtration and removal of solvent gave an oil which was applied to a silica gel column (eluent: methylene chloride) giving 34.5 g of benzo[b]thiophen-3-ylethanol as an oil.

Workup

  1. temperatureby reflux for 1 h
  2. customHydrolysis
  3. filtrationwith water, filtration and removal of solvent
  4. customgave an oil which

Sources & evidence

ORD record
ord-00ca2e0543264fd58716ee479b885f1a
Source dataset
uspto-grants-2000_02
Patent number
US06031099

Reaction notes

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