Ethyl propiolate → HCID 86652418, compound

HRID 1040402Notes

Reaction equation

HRID 1040402 reaction equation
[N:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])=[N+:2]=[N-:3].[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[C:13]#[CH:14]>CN(C)C=O.C(OCC)(=O)C.CCCCCC>[CH:6]([C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N:1]1[CH:14]=[C:13]([C:12]([O:16][CH2:17][CH3:18])=[O:15])[N:3]=[N:2]1)=[O:7].[CH:6]([C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N:1]1[C:13]([C:12]([O:16][CH2:17][CH3:18])=[O:15])=[CH:14][N:3]=[N:2]1)=[O:7]

Participants

7

Reactant 2

HCID 12182Ethyl propiolate2×HCID 108880602-azidobenzaldehyde

Product 2

HCID 86652418HCID 86652418, compoundYield 66%HCID 86652419HCID 86652419, compoundYield 17%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-azidobenzaldehyde (100 mg, 0.68 mmol) in 1.0 mL of dry N,N-dimethylformamide was added ethyl propiolate (0.14 mL, 1.4 mmol) at room temperature. After being stirred at 100° C. for 12 h, ethyl propiolate (0.14 mL, 1.4 mmol) was added again with additional stirring for 12 h. After cooling, the reaction mixture was diluted with a 5:1 solution (12 mL) of ethyl acetate and hexane. The solution was washed with water twice, brine, and dried over Na2SO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified with silica gel column chromatography (hexane/ethyl acetate=90/10 to 75/25) to obtain ethyl 1-(2-formylphenyl)-1H-1,2,3-triazol-4-carboxylate as a crystal (111 mg, 66%) and ethyl 1-(2-formylphenyl)-1H-1,2,3-triazol-5-carboxylate as a oil (28 mg, 17%).

Workup

  1. stirringwith additional stirring for 12 h
  2. temperatureAfter cooling
  3. washThe solution was washed with water twice
  4. dry with materialbrine, and dried over Na2SO4
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated in vacuo
  7. customthe residue was purified with silica gel column chromatography (hexane/ethyl acetate=90/10 to 75/25)

Sources & evidence

ORD record
ord-b8c4a077bec34deb85e99db9cd3bb316
Source dataset
uspto-grants-2013_10
Patent number
US08552220B2

Reaction notes

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