Ethyl cyanoacetate → HCID 72326551, compound

HRID 1176808Notes

Reaction equation

HRID 1176808 reaction equation
C(N(CC)CC)C.[C:8]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])#[N:9].[CH2:16]([CH:18]([CH2:22][CH3:23])[C:19](Cl)=[O:20])[CH3:17]>C(#N)C>[C:8]([C:10](=[C:19]([OH:20])[CH:18]([CH2:22][CH3:23])[CH2:16][CH3:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])#[N:9]

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 8471TriethylamineHCID 759542-Ethylbutyryl chloride

Product 1

HCID 72326551HCID 72326551, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

With ice-cooling, 227 g (2.15 mol) of triethylamine were poured into a solution of 170 g (1.5 mol) of ethyl cyanoacetate in acetonitrile, and 101 g (0.75 mol) of 2-ethylbutyryl chloride were added dropwise at from 10 to 25° C. After 2 h of stirring at 25° C., the mixture was concentrated and the residue was dissolved in MTBE (methyl tert-butyl ether). By washing with 5% strength NaOH, the enolate was transferred into the aqueous phase, from which it was released by acidification to pH 3. The acidic aqueous solution was extracted and the extract was dried and concentrated. Customary purification gave 100 g (63% of theory) of the title compound as an oil (b.p. 78 to 80° C./1.5 mbar).

Workup

  1. temperatureWith ice-cooling
  2. additionwere added dropwise at from 10 to 25° C
  3. concentrationthe mixture was concentrated
  4. dissolutionthe residue was dissolved in MTBE (methyl tert-butyl ether)
  5. washBy washing with 5% strength NaOH
  6. extractionThe acidic aqueous solution was extracted
  7. customthe extract was dried
  8. concentrationconcentrated
  9. customCustomary purification

Sources & evidence

ORD record
ord-5c8e72f4dd454b7dadd674343fe11975
Source dataset
uspto-grants-2010_11
Patent number
US07842832B2

Reaction notes

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