Allyl chloroformate → HCID 54299807, compound

HRID 1283755Notes

Reaction equation

HRID 1283755 reaction equation
[Na].[OH:2][N:3]=[C:4]([C:10]#[N:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14].C(=O)([O-])O.[Na+]>O.C(OCC)(=O)C>[CH2:16]([O:15][C:13]([O:2][N:3]=[C:4]([C:10]#[N:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:14])[CH:17]=[CH2:18]

Participants

7

Reactant 4

HCID 18052Allyl chloroformateHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetate

Product 1

HCID 54299807HCID 54299807, compoundYield 62.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of sodium salt of ethyl 2-hydroxyimino-2-cyanoacetate (23.1 g) in water (100 ml), a solution of allyl chloroformate (17.0 g) in ethyl acetate (30 ml) is dropwise added at 5° to 10°C. The resulting mixture is stirred for 1 hour while adjusting pH to 7 with the addition of an aqueous solution of sodium hydrogencarbonate. The reaction mixture is extracted with ethyl acetate, and the organic layer is washed with water, dried and concentrated. The residue is distilled under reduced pressure to give ethyl 2-allyloxycarbonyloxyimino-2-cyanoacetate (19.9 g) as an oil. B.P. 122 to 124°C/0.9 mmHg.

Workup

  1. extractionThe reaction mixture is extracted with ethyl acetate
  2. washthe organic layer is washed with water
  3. customdried
  4. concentrationconcentrated
  5. distillationThe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-03103ca208c446d7b8703605e757cab5
Source dataset
uspto-grants-1976_08
Patent number
US03976635

Reaction notes

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