Pyridine → Ethyl 3-(2-phenyl-1-cyclopropyl)-3-oxo-propanoate

HRID 231123

Reaction equation

HRID 231123 reaction equation
[C:1]1([CH:7]2[CH2:9][CH:8]2[C:10](Cl)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13][C:14]1(C)[O:19]C(=O)[CH2:17][C:16](=O)[O:15]1.N1C=CC=CC=1.OS(O)(=O)=O>ClCCCl.O>[C:1]1([CH:7]2[CH2:9][CH:8]2[C:10](=[O:11])[CH2:13][C:14]([O:15][CH2:16][CH3:17])=[O:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 1118Sulfuric AcidHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 523092Cyclopropanecarbonyl chloride, 2-phenyl-

Product 1

HCID 20034593Ethyl 3-(2-phenyl-1-cyclopropyl)-3-oxo-propanoateYield 108.9%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolvent

Procedure

A solution of 2-phenyl-1-cyclopropanecarboxylic acid chloride (15 g) in 1,2-dichloroethane (70 ml) is added at 0° C. to a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum's acid, 12 g) and pyridine (13.2 g) in 1,2-dichloroethane (70 ml) and the solution is stirred at room temperature for one hour. A 2N water solution of H2SO4 (20 ml) is then added, the two layers are separated and the organic phase is washed twice with water (50 ml), dryed on Na2SO4 and evaporated in vacuum. The residue is dissolved in EtOH (150 ml), heated to the reflux temperature for two hours and evaporated to dryness to give almost pure ethyl 3-(2-phenyl-1-cyclopropyl)-3-oxo-propanoate (21 g).

Workup

  1. customthe two layers are separated
  2. washthe organic phase is washed twice with water (50 ml)
  3. customevaporated in vacuum
  4. dissolutionThe residue is dissolved in EtOH (150 ml)
  5. temperatureheated to the reflux temperature for two hours
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-7865c18e0e4847a6b3d2252f1c412f04
Source dataset
uspto-grants-1989_07
Patent number
US04845113

Linked notes

Loading…