1-Methylimidazole → Ethyl 2-methyl-2-[6-(trifluoromethyl)pyridin-3-yl]cyclopropanecarboxylate

HRID 607502Notes

Reaction equation

HRID 607502 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([F:13])([F:12])[F:11])=[N:8][CH:9]=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]=[N:8][C:7]([C:10]([F:13])([F:12])[F:11])=[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 576623365-(Prop-1-en-2-yl)-2-(trifluoromethyl)pyridine

Product 1

HCID 67046940Ethyl 2-methyl-2-[6-(trifluoromethyl)pyridin-3-yl]cyclopropanecarboxylateYield 63%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A toluene (2 ml) solution of 5-isopropenyl-2-(trifluoromethyl)pyridine (219 mg, 1.17 mmol), Co(TPP) (26 mg, 0.039 mmol) and 1-methyl-1H-imidazole (320 mg, 3.9 mmol), ethyl diazoacetate (208 mg, 1.8 mmol) were treated in the same procedure as described in Example 2H. The crude residue (201 mg, 63% yield of the title compound as a black oil) was used in a further reaction without purification.

Sources & evidence

ORD record
ord-8e4ec3418cb74890a43b1816c4a84b3b
Source dataset
uspto-grants-2011_03
Patent number
US07915448B2

Reaction notes

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