2-Acetyl-5-methylthiophene → 1-(5-Methyl-2-thienyl)ethanol

HRID 911348

Reaction equation

HRID 911348 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[S:7][C:8]([CH3:11])=[CH:9][CH:10]=1)(=[O:5])[CH3:4]>CO>[OH:5][CH:3]([C:6]1[S:7][C:8]([CH3:11])=[CH:9][CH:10]=1)[CH3:4]

Participants

4

Reactant 2

HCID 836552-Acetyl-5-methylthiopheneHCID 4311764Sodium borohydride

Product 1

HCID 150917951-(5-Methyl-2-thienyl)ethanolYield 98.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add sodium borohydride (270 mg, 7.13 mmol) to a solution of 2-acetyl-5-methylthiophene (1.0 g, 7.13 mmol) in methanol (40 mL). Stir the mixture for 1 h at room temperature. Remove the solvent in vacuo and partition the residue between water and DCM. Separate the organic phase, dry over Na2SO4, filter and concentrate to obtain the desired intermediate as an oil (0.995 g, 98%) that was used without further purification. GC-MS m/z 142 (M+).

Workup

  1. customRemove the solvent in vacuo
  2. custompartition the residue between water and DCM
  3. customSeparate the organic phase
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-35e11b1c7cc242e69b94091dbc8564d5
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Linked notes

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