Ethyl diazoacetate → Ethyl 2-tert-butoxy-3-(5-methylpyridin-2-yl)cyclopropanecarboxylate

HRID 2175421Notes

Reaction equation

HRID 2175421 reaction equation
[C:1]([O:5]/[CH:6]=[CH:7]\[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[N+](=[CH:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N-]>C1(C)C=CC=CC=1.S([O-])([O-])(=O)=O.[Cu+2]>[C:1]([O:5][CH:6]1[CH:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][N:9]=2)[CH:17]1[C:18]([O:20][CH2:21][CH3:22])=[O:19])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 12192Ethyl diazoacetateHCID 86729575(Z)-2-(2-tert-butoxyvinyl)-5-methylpyridine

Product 1

HCID 71271320Ethyl 2-tert-butoxy-3-(5-methylpyridin-2-yl)cyclopropanecarboxylateYield 34%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 1140TolueneSolvent2×

Procedure

The solution of (Z)-2-(2-tert-butoxyvinyl)-5-methylpyridine (12-3) (1.20 g, 6.27 mmol) in toluene (20 mL) and anhydrous copper sulfate (100 mg, 0.63 mmol) was heated to 75° C. Then the solution of ethyl diazoacetate (2.17 g, 18.8 mmol) in toluene (10 mL) was added dropwise over 2 h. It was heated for another 2 h after the addition was completed. The mixture was restored to room temperature for overnight. The solvent was removed under reduced pressure and the residue was purified by silca gel chromatography with gradient eluent (PE/EA=40/1; 20/1; 10/1). The product was obtained as a yellow oil (500 mg, 34%). LRMS (ES) calculated M+H for C16H24NO3: 278.3. Found: 278.2.

Workup

  1. temperatureIt was heated for another 2 h
  2. additionafter the addition
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by silca gel chromatography with gradient eluent (PE/EA=40/1; 20/1; 10/1)

Sources & evidence

ORD record
ord-99e517fbd9d048e5ab1d10103465dc69
Source dataset
uspto-grants-2015_06
Patent number
US09062059B2

Reaction notes

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