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

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

Reactant 4

HCID 6344Dichloromethane

HCID 8028Tetrahydrofuran2×

HCID 238124Methyl 2-(1-benzothiophen-3-yl)acetate

HCID 21226445Aluminium lithium hydride

Product 1

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

Procedure

A solution of methyl benz[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 5 silica gel column (eluent: methylene chloride) giving 34.5 g of benzo[b]thiophen-3-ylethanol as an oil.