Dimethylformamide → Ethyl 2-cyanocyclopropane-1-carboxylate

HRID 561410Notes

Reaction equation

HRID 561410 reaction equation
C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[C:12](#[N:15])[CH:13]=[CH2:14].Cl[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[C:12]([CH:13]1[CH2:14][CH:17]1[C:18]([O:20][CH2:21][CH3:22])=[O:19])#[N:15]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7751Ethyl chloroacetateHCID 7855AcrylonitrileHCID 11430Potassium Carbonate

Product 1

HCID 286692Ethyl 2-cyanocyclopropane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

40.2 g (291 mmol) of potassium carbonate were introduced into 89 ml of DMF at RT, 9.6 ml (146 mmol) of acrylonitrile, 15.5 ml (146 mmol) of ethyl chloroacetate and 1.96 g (8.61 mmol) of benzyltriethylammonium chloride were added, and the mixture was stirred at RT for 3 days. Water was added, the mixture was extracted with diethyl ether, and the combined organic phases were dried over sodium sulfate, filtered and concentrated. The residue was purified by vacuum distillation. 6.50 g (30% of theory) of the title compound (boiling range: 63-66° C./0.9 mbar) and 1.41 g (7%) of the corresponding cis-isomer (boiling range: 85-89° C./0.9 mbar) were obtained.

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. dry with materialthe combined organic phases were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. distillationThe residue was purified by vacuum distillation

Sources & evidence

ORD record
ord-9b31c226ea4547819ceab208b01e6ab2
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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