Methanol → HCID 67046961, compound

HRID 1438404Notes

Reaction equation

HRID 1438404 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][CH:5]=1)=[O:3].[CH:14](OC)(OC)[O:15]C.[CH3:21]O>[Br-].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:21][O:3][C:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:11])([F:12])[F:13])=[CH:6][CH:5]=1)([O:15][CH3:14])[CH3:1]

Participants

5

Reactant 3

HCID 887MethanolHCID 9005Trimethyl orthoformateHCID 697311-(4-(Trifluoromethyl)phenyl)ethan-1-one

Product 1

HCID 67046961HCID 67046961, compound

Reagents, catalysts & solvents 1

HCID 23500184Tetra-n-butylammonium tribromideCatalyst

Procedure

To a stirred solution of 4-(trifluoromethyl)acetophenone (purchased from Aldrich, 3.76 g, 20 mmol) in MeOH (3 ml) was added trimethyl orthoformate (2.33 g, 22 mmol) and tetrabutylammonium tribromide (96.4 mg, 0.2 mmol) successively. The mixture was stirred at room temperature for 24 hours, quenched with saturated aqueous sodium bicarbonate, and extracted with diethyl ether. The organic layer was washed with brine and dried over sodium sulfate. The mixture was filtered and concentrated in vacuo to afford the crude title compound (5.95 g) as a colorless oil.

Workup

  1. customquenched with saturated aqueous sodium bicarbonate
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e5ed2af532f3400ab9c8b2dc57a70538
Source dataset
uspto-grants-2009_11
Patent number
US07622589B2

Reaction notes

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