Acetic Acid → HCID 57172719, compound

HRID 2187345Notes

Reaction equation

HRID 2187345 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].C(O)(=O)C.N1[CH2:18][CH2:17][CH2:16][CH2:15]C1>C1(C)C=CC=CC=1>[C:1]([C:3](=[CH:15][CH:16]1[CH2:18][CH2:17]1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 8082Piperidine

Product 1

HCID 57172719HCID 57172719, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 14 g (0.2 mol) of cyclopropylcarbaldehyde, 22.6 g (0.2 mol) of ethyl cyanoacetate, 1.4 ml of glacial acetic acid and 0.4 ml of piperidine in 200 ml of toluene was refluxed for 6 hours. After cooling, the mixture was washed with in each case 300 ml of 10% strength hydrochloric acid and water. The organic phase was dried and concentrated and the residue was subjected to distillation in vacuo. This gave 14.2 g (yield 43%) of ethyl 2-cyano-3-cyclopropyl-2-propenoate (b.p. 95° C./0.3 mbar).

Workup

  1. temperatureAfter cooling
  2. washthe mixture was washed with in each case 300 ml of 10% strength hydrochloric acid and water
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. distillationthe residue was subjected to distillation in vacuo

Sources & evidence

ORD record
ord-4263675a1baa45019a8c19d902bfee6d
Source dataset
uspto-grants-2002_06
Patent number
US06410486B1

Reaction notes

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