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

HRID 1377491Notes

Reaction equation

HRID 1377491 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. The product was dissolved in 200 ml of methylene chloride, thionyl chloride (20 ml) was added followed by reflux for 5 h. Removal of solvent and excess thionyl chloride in vacuo gave 3-(2-chloro-1-ethyl)-benzo[b]thiophene as an oil (45 g). The chloride was converted to 4-benzo[b]thiophen-3-yl-1-butanol via treatment with dimethyl malonate followed by hydrolysis, decarboxylation and reduction according to the method described in EXAMPLE 11. The title compound 10a was prepared from 4-benzo[b]thiophen-3-yl-1-butanol and spiro[isobenzofuran-1(3H),4'-piperidine] by the method described in EXAMPLE 2. Yield: 2.2 g, mp: 144°-45° C.

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-bbb7b0a114604338b600fa3bf7658b92
Source dataset
uspto-grants-1997_09
Patent number
US05665725

Reaction notes

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