Ethyl cyanoacetate → HCID 86647124, compound

HRID 1801437Notes

Reaction equation

HRID 1801437 reaction equation
[CH3:1][CH:2]([CH2:7][CH:8]([CH3:10])[CH3:9])[CH2:3][C:4](=O)[CH3:5].[C:11]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:12].C([O-])(=O)C.[NH4+].CC1CCCCC1>O.C(O)(=O)C>[C:14]([C:13](=[C:4]([CH3:5])[CH2:3][CH:2]([CH3:1])[CH2:7][CH:8]([CH3:10])[CH3:9])[C:11]#[N:12])([O:16][CH2:17][CH3:18])=[O:15]

Participants

7

Reactant 4

HCID 7764Ethyl cyanoacetateHCID 7962MethylcyclohexaneHCID 891804,6-Dimethyl-2-heptanoneHCID 517165Ammonium Acetate

Product 1

HCID 86647124HCID 86647124, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A 250 ml round-bottom flask equipped with a Dean-Stark apparatus is charged in succession with 25.6 g of 4,6-dimethylheptanone (0.18 mol), 14.34 g of ethyl cyanoacetate (0.127 mol), 1.95 g of ammonium acetate, 6 g of acetic acid, and 100 ml of methylcyclohexane. The mixture is heated to reflux, the water formed being separated off as it is formed. After one hour, the mixture is cooled to ambient temperature and then washed to neutrality with saturated sodium bicarbonate solution. The residue is distilled under vacuum (6 torr) for recovery of the excess ketone (6.5 g) and then under a high vacuum for isolation of the cyano ester VI. 25.8 g of a colorless liquid are collected (b.p.=100-104° C./2.10−1 torr), corresponding to a yield of 85%.

Workup

  1. customA 250 ml round-bottom flask equipped with a Dean-Stark apparatus
  2. temperatureThe mixture is heated
  3. temperatureto reflux
  4. custombeing separated off as it
  5. customis formed
  6. washwashed
  7. distillationThe residue is distilled under vacuum (6 torr) for recovery of the excess ketone (6.5 g)
  8. custom25.8 g of a colorless liquid are collected (b.p.=100-104° C./2.10−1 torr)

Sources & evidence

ORD record
ord-ec06a6cc2d704d4b81ebc903d49d41f5
Source dataset
uspto-grants-2013_01
Patent number
US08349790B2

Reaction notes

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