Toluene → Ethyl 2-[6-tert-butylpyridin-3-yl]-2-ethylcyclopropanecarboxylate

HRID 1438403Notes

Reaction equation

HRID 1438403 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5]C=[CH:3][CH:2]=1.CN1[CH:13]=[CH:12][N:11]=[CH:10]1.[N+](=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N-]>CCOC(C)=O>[C:1]([C:12]1[N:11]=[CH:10][C:6]([C:1]2([CH2:2][CH3:3])[CH2:7][CH:16]2[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:5][CH:13]=1)([CH3:7])([CH3:6])[CH3:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 13901-MethylimidazoleHCID 12192Ethyl diazoacetate

Product 1

HCID 67046826Ethyl 2-[6-tert-butylpyridin-3-yl]-2-ethylcyclopropanecarboxylateYield 49%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a toluene (100 ml) solution of the compound of example 62B (1.89 g, 10 mmol), Co(TPP) (0.17 g, 0.25 mmol), 1-methyl-1H-imidazole (2.39 ml, 30 mmol), and ethyl diazoacetate (1.58 ml, 15 mmol) were added and the mixture was stirred for 5 minutes at room temperature followed by additional stirring for 1.5 hours at 80° C. The reaction mixture was diluted with EtOAc and washed with saturated aqueous sodium bicarbonate. The organic layer was dried over sodium sulfate and concentrated in vacuo to give the crude product. The crude product was purified by column chromatography on silica gel, eluting with hexane/EtOAc (1:10), to give the title compound (1.34 g, 49%, trans) as a brown oil.

Workup

  1. stirringby additional stirring for 1.5 hours at 80° C
  2. washwashed with saturated aqueous sodium bicarbonate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give the crude product
  6. customThe crude product was purified by column chromatography on silica gel
  7. washeluting with hexane/EtOAc (1:10)

Sources & evidence

ORD record
ord-b0f855967a7049d2844c4284b812b4b6
Source dataset
uspto-grants-2009_11
Patent number
US07622589B2

Reaction notes

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