N,N-Diethyl-2-(trifluoromethoxy)-4-vinylbenzamide → N,N-diethyl-4-ethyl-2-(trifluoromethoxy)benzamide

HRID 1296274Notes

Reaction equation

HRID 1296274 reaction equation
[CH2:1]([N:3]([CH2:19][CH3:20])[C:4](=[O:18])[C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH2:12])=[CH:7][C:6]=1[O:13][C:14]([F:17])([F:16])[F:15])[CH3:2].[H][H]>[Pd].CO>[CH2:19]([N:3]([CH2:1][CH3:2])[C:4](=[O:18])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH3:12])=[CH:7][C:6]=1[O:13][C:14]([F:16])([F:15])[F:17])[CH3:20]

Participants

5

Reactant 2

HCID 68691199N,N-Diethyl-2-(trifluoromethoxy)-4-vinylbenzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 68690487N,N-diethyl-4-ethyl-2-(trifluoromethoxy)benzamideYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirring degassed solution of N,N-diethyl-4-ethenyl-2-(trifluormethoxy)benzamide (1783 mg, 6.2 mmol) and 10% palladium on carbon (50 mg) in MeOH (30 mL) was added hydrogen (1 atm). The reaction was stirred for 1 h and then filtered. The filtrate was conc. in vacuo to a colorless oil. The oil was purified by flash chromatography (SiO2, 0–50% EtOAc in hexanes) to give 1489 mg of the desired product as a colorless oil. MS (ESI) 290 (M+H).

Workup

  1. filtrationfiltered
  2. customThe oil was purified by flash chromatography (SiO2, 0–50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-1b0744e0f6344db2bef58523dbe3366d
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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