Aluminium lithium hydride → (5-Chloro-1-benzothiophen-2-yl)methanol

HRID 27928Notes

Reaction equation

HRID 27928 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[S:15][C:14]([C:16](OC)=[O:17])=[CH:13][C:12]=2[CH:20]=1>CCOCC>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[S:15][C:14]([CH2:16][OH:17])=[CH:13][C:12]=2[CH:20]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 23340399Methyl 5-chloro-1-benzothiophene-2-carboxylate

Product 1

HCID 23340421(5-Chloro-1-benzothiophen-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To lithium aluminum hydride (26.5 mmol) and 50 ml ether, at -20° under nitrogen, is slowly added methyl 5-chlorobenzothiophene-2-carboxylate (6 g, 26.5 mmol). The mixture is then stirred at -20° for 10 minutes. After no starting material is detectable by thin layer chromatography, the mixture is quenched with 1 ml water, 1 ml 15% NaOH, and 3 ml water at -20°. The mixture is allowed to warm to RT and stirred for 15 hours. The mixture was then filtered and solvent evaporated to give 5-chlorobenzothiophene-2-methanol.

Workup

  1. customat -20°
  2. customthe mixture is quenched with 1 ml water, 1 ml 15% NaOH, and 3 ml water at -20°
  3. stirringstirred for 15 hours
  4. filtrationThe mixture was then filtered
  5. customsolvent evaporated

Sources & evidence

ORD record
ord-fdfe5cd99fe6490e97605364335359ff
Source dataset
uspto-grants-1980_09
Patent number
US04224330

Reaction notes

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