1-Methylimidazole → Ethyl 2-(6-tert-butylpyridin-3-yl)cyclopropanecarboxylate

HRID 1438379Notes

Reaction equation

HRID 1438379 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([CH3:13])=[CH2:12])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].CN1C=CN=C1.[N+](=C[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N-]>C1(C)C=CC=CC=1>[C:1]([C:5]1[N:6]=[CH:7][C:8]([CH:11]2[CH2:13][CH:12]2[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 13901-MethylimidazoleHCID 12192Ethyl diazoacetateHCID 670465842-Tert-butyl-5-isopropenylpyridine

Product 1

HCID 67046620Ethyl 2-(6-tert-butylpyridin-3-yl)cyclopropanecarboxylateYield 41.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a toluene (60 ml) solution of 2-tert-butyl-5-isopropenylpyridine (5.96 g, 34 mmol), Co(TPP) (0.69 g, 1.0 mmol) and 1-methyl-1H-imidazole (8.37 g, 102 mmol), ethyl diazoacetate (5.4 g, 48 mmol) was added and the mixture was stirred for 5 minutes at room temperature followed by additional stirring for 1 hour at 80° C. Then, evaporation of the solvent and purification by silica gel column chromatography, eluting with gradually from hexane to hexane/ethylacetate (30:1), gave the title compound (3.51 g, 39%, trans) as white solids.

Workup

  1. stirringby additional stirring for 1 hour at 80° C
  2. customThen, evaporation of the solvent and purification by silica gel column chromatography
  3. washeluting with gradually from hexane to hexane/ethylacetate (30:1)

Sources & evidence

ORD record
ord-24f8c681e5424e208adebf4a593b4e87
Source dataset
uspto-grants-2009_11
Patent number
US07622589B2

Reaction notes

Loading…