Methanol → HCID 67046961, compound

HRID 607526Notes

Reaction equation

HRID 607526 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-1ef1e355c9634dc4a2f4120bf52b6091
Source dataset
uspto-grants-2011_03
Patent number
US07915448B2

Reaction notes

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