Diethyl Ether → 3-Propyl-6-(trifluoromethyl)benzothiophene-2-carboxaldehyde

HRID 241368Notes

Reaction equation

HRID 241368 reaction equation
[CH2:1]([C:4]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:7]=2[S:6][C:5]=1[CH2:17][OH:18])[CH2:2][CH3:3].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.CCOCC>ClCCl>[CH2:1]([C:4]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]([F:15])([F:16])[F:14])=[CH:12][C:7]=2[S:6][C:5]=1[CH:17]=[O:18])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 66883667[3-Propyl-6-(trifluoromethyl)-benzothiophen-2-yl]methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 866528643-Propyl-6-(trifluoromethyl)benzothiophene-2-carboxaldehydeYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of [3-propyl-6-(trifluoromethyl)-benzothiophen-2-yl]methanol (126 mg, 0.459 mmol) and powdered Molecular sieves 3A (250 mg) in dichloromethane (2.3 mL) was added pyridinium chlorochromate (198 mg, 0.919 mmol). The mixture was stirred for 40 minutes at room temperature, to which was added ether (20 mL) and silica gel (Wakogel C-300HG, 2 g). The mixture was stirred for 10 minutes at room temperature, and filtered. The filtered cake was washed out with ether. The filtrate and washings were combined, and concentrated to give the titled compound as a brown crystal (112 mg, yield 90%).

Workup

  1. stirringThe mixture was stirred for 10 minutes at room temperature
  2. filtrationfiltered
  3. washThe filtered cake was washed out with ether
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5a34341640844a14b6ddc992e2732d76
Source dataset
uspto-grants-2014_02
Patent number
US08648208B2

Reaction notes

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