Ethyl diazoacetate → HCID 178468948, compound

HRID 129831

Reaction equation

HRID 129831 reaction equation
[CH3:1][C:2](=[O:5])[C:3]#[CH:4].[N+:6](=[CH:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N-:7]>CCOCC>[CH2:12]([O:11][C:9]([C:8]1[CH:4]=[C:3]([C:2](=[O:5])[CH3:1])[NH:7][N:6]=1)=[O:10])[CH3:13]

Participants

4

Reactant 2

HCID 12192Ethyl diazoacetateHCID 15018Butyn-2-one

Product 1

HCID 178468948HCID 178468948, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A 500 ml Erlenmeyer flask was charged with 25.0 g of 3-butyne-2-one and ethyl ether (200 ml). To the resulting solution, 41.9 g of ethyl diazoacetate were added slowly with stirring. After 30 minutes of stirring, the ether solution began refluxing by itself. After stirring for 1 hour, the mixture was chilled at 0° C. for 1 hour and filtered to yield 28.5 g of 5-acetylpyrazole-3-carboxylic acid ethyl ester as white solids, mp 114°-115° C. NMR: 1.42 (t, 3H), 2.62 (s, 3H), 4.44 (q, 2H), 7.36 (s, 1H).

Workup

  1. stirringAfter 30 minutes of stirring
  2. stirringAfter stirring for 1 hour
  3. filtrationfiltered

Sources & evidence

ORD record
ord-944a8efdff484e2dbd12857c45c920c5
Source dataset
uspto-grants-1995_11
Patent number
US05470862

Linked notes

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