1-{3-Methyl-5-[4-(trifluoromethyl)phenyl]thien-2-yl}ethanol → 1-[3-Methyl-5-(4-trifluoromethyl-phenyl)-thiophen-2-yl]-ethanone

HRID 1785235

Reaction equation

HRID 1785235 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)[S:4][C:3]=1[CH:17]([OH:19])[CH3:18]>O=[Mn]=O>[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:13]([F:16])([F:14])[F:15])=[CH:11][CH:12]=2)[S:4][C:3]=1[C:17](=[O:19])[CH3:18]

Participants

3

Reactant 1

HCID 219863591-{3-Methyl-5-[4-(trifluoromethyl)phenyl]thien-2-yl}ethanol

Product 1

HCID 575950001-[3-Methyl-5-(4-trifluoromethyl-phenyl)-thiophen-2-yl]-ethanone

Reagents, catalysts & solvents 1

HCID 14801Manganese dioxideCatalyst2×

Procedure

To a solution of 1-[3-Methyl-5-(4-trifluoromethyl-phenyl)-thiophen-2-yl]-ethanol (see Preparation 2)(4.40 g, 15.4 mmole), is added MnO2 (7.88 g, 77.0 mmole) in one portion. The mixture is heated under reflux for 16 hours, more MnO2 (7.88 g, 77.0 mmole) is added to the reaction and continued to reflux for 4 hours. The mixture is filtered through a celite pad, and the mother liquid is concentrated. The crude product is purified on a silica gel column, gradient eluting with 0-20% ethyl acetate in hexane and concentrated to provide the titled compound as yellow solid.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 16 hours
  3. temperatureto reflux for 4 hours
  4. filtrationThe mixture is filtered through a celite pad
  5. concentrationthe mother liquid is concentrated
  6. customThe crude product is purified on a silica gel column
  7. washgradient eluting with 0-20% ethyl acetate in hexane
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-617d2c25a5ed444db23b3ce802b6ae6c
Source dataset
uspto-grants-2009_03
Patent number
US07504433B2

Linked notes

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