Cornforth reagent → 1-(5-Methyl-2-thienyl)-2-propanone

HRID 2081753Notes

Reaction equation

HRID 2081753 reaction equation
[CH3:1][C:2]1[S:6][C:5]([CH:7](O)[CH2:8][CH3:9])=[CH:4][CH:3]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:12].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH3:1][C:2]1[S:6][C:5]([CH2:7][C:8](=[O:12])[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 19780497α-Ethyl-5-methyl-2-thiophenemethanol

Product 1

HCID 158529041-(5-Methyl-2-thienyl)-2-propanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(5-methylthien-2-yl)propanol from above (20 mmol) and pyridinium dichromate (9.03 g, 24 mmol) in 100 mL CH2Cl2 was stirred for 18 h. The reaction was then filtered through Celite and the filtrate was concentrated. The resulting residue was purified by chromatography (silica gel, etherhexanes, 1:9) to afford 1.86 g (60% over the two steps) of the desired product.

Workup

  1. filtrationThe reaction was then filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. customThe resulting residue was purified by chromatography (silica gel, etherhexanes, 1:9)

Sources & evidence

ORD record
ord-c3bd5dd98b674a9b85532ccd407a99bc
Source dataset
uspto-grants-1993_02
Patent number
US05185363

Reaction notes

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