2-Ethylbutyryl chloride → HCID 72326551, compound

HRID 1176807Notes

Reaction equation

HRID 1176807 reaction equation
[CH2:1]([CH:3]([CH2:7][CH3:8])[C:4](Cl)=[O:5])[CH3:2].[CH2:9]([O:11][C:12](=[O:16])[CH2:13][C:14]#[N:15])[CH3:10].[Na]>C(OCC)C>[C:14]([C:13](=[C:4]([OH:5])[CH:3]([CH2:7][CH3:8])[CH2:1][CH3:2])[C:12]([O:11][CH2:9][CH3:10])=[O:16])#[N:15]

Participants

4

Reactant 2

HCID 759542-Ethylbutyryl chlorideHCID 86596802HCID 86596802, compound

Product 1

HCID 72326551HCID 72326551, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
25 °C

Procedure

At 0° C., 74 g (0.55 mol) of 2-ethylbutyryl chloride were added dropwise to a suspension of 150 g (1.1 mol) of sodium cyanoacetate ethyl ester in diethyl ether. The reaction mixture was stirred at 25° C. for 16 h and then hydrolyzed, and the organic phase was separated off. The aqueous phase was washed with ether and then acidified to pH 3. The enol released in this manner was extracted, washed and dried. Customary purification gave 81 g (70% of theory) of the title compound as a viscous colorless liquid (b.p. 78 to 81° C./1.2 mbar).

Workup

  1. customhydrolyzed, and the organic phase was separated off
  2. washThe aqueous phase was washed with ether
  3. extractionwas extracted
  4. washwashed
  5. customdried
  6. customCustomary purification

Sources & evidence

ORD record
ord-02edac165973445e9fe101c0be58a37e
Source dataset
uspto-grants-2010_11
Patent number
US07842832B2

Reaction notes

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