1-Methylimidazole → Ethyl 2-methyl-2-[4-(trifluoromethyl)phenyl]cyclopropanecarboxylate

HRID 607504Notes

Reaction equation

HRID 607504 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][CH:5]=1)([CH3:3])=[CH2:2].CN1C=CN=C1.[N+](=[CH:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N-]>C1(C)C=CC=CC=1>[CH3:3][C:1]1([C:4]2[CH:9]=[CH:8][C:7]([C:10]([F:11])([F:13])[F:12])=[CH:6][CH:5]=2)[CH2:2][CH:22]1[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

5

Reactant 3

HCID 13901-MethylimidazoleHCID 12192Ethyl diazoacetateHCID 5215861-Isopropenyl-4-(trifluoromethyl)benzene

Product 1

HCID 67047022Ethyl 2-methyl-2-[4-(trifluoromethyl)phenyl]cyclopropanecarboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a toluene (50 ml) solution of 1-isopropenyl-4-(trifluoromethyl)benzene (4.93 g, 26.5 mmol) [Tetrahedron (2003), 59(17), 2999-3002], Co(TPP) (534 g, 0.795 mmol) and 1-methyl-1H-imidazole (6.53 g, 79.5 mmol), ethyl diazoacetate (4.23 g, 37.0 mmol) was added. Then the reaction and the following work-up were carried out according to the procedure described in Example 2H. The crude residue was applied to a silica gel chromatography column and eluted with a volume mixture of hexane and EtOAc (20/1) to afford 5.92 g (82% yield, trans) of the title compound as a colorless oil.

Workup

  1. customThen the reaction
  2. washeluted with a volume mixture of hexane and EtOAc (20/1)

Sources & evidence

ORD record
ord-3a90af0520b54c0fad4b7896e39f8995
Source dataset
uspto-grants-2011_03
Patent number
US07915448B2

Reaction notes

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