Water → Ethyl 2-t-amyloxycarbonyloxyimino-2-cyanoacetate

HRID 1283762Notes

Reaction equation

HRID 1283762 reaction equation
Cl[C:2]([O:4][C:5]([CH2:8][CH3:9])([CH3:7])[CH3:6])=[O:3].[OH:10][N:11]=[C:12]([C:18]#[N:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14].C(N(CC)CC)C.O>C1C=CC=CC=1>[C:5]([O:4][C:2]([O:10][N:11]=[C:12]([C:18]#[N:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:3])([CH2:8][CH3:9])([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetateHCID 15051328Carbonochloridic acid, 1,1-dimethylpropyl ester

Product 1

HCID 54231162Ethyl 2-t-amyloxycarbonyloxyimino-2-cyanoacetateYield 39.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of t-amyl chloroformate (0.05 mol) in an ether-toluene mixture (30 ml) is cooled to -10°C, and a solution of ethyl 2-hydroxyimino-2-cyanoacetate (7.2 g) and triethylamine (7.0 ml) in dry benzene (50 ml) is dropwise added thereto. The resulting mixture is allowed to stand at room temperature over night. The reaction mixture is admixed with water and filtered. The organic layer is separated, washed with water, dried and concentrated to give ethyl 2-t-amyloxycarbonyloxyimino-2-cyanoacetate (5.1 g) as an oil.

Workup

  1. waitto stand at room temperature over night
  2. filtrationfiltered
  3. customThe organic layer is separated
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-be9f8bf8203142aeaadbd6558865471f
Source dataset
uspto-grants-1976_08
Patent number
US03976635

Reaction notes

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