Ethyl propiolate → ethyl 1H-1,2,3-triazole-4-carboxylate

HRID 244663Notes

Reaction equation

HRID 244663 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[C:2]#[CH:3].C[Si]([N:12]=[N+:13]=[N-:14])(C)C>CO>[N:12]1[NH:13][N:14]=[C:2]([C:1]([O:5][CH2:6][CH3:7])=[O:4])[CH:3]=1

Participants

4

Reactant 2

HCID 12182Ethyl propiolateHCID 78378Azidotrimethylsilane

Product 1

HCID 6419107ethyl 1H-1,2,3-triazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 2-propynoate (4.13 ml) and trimethylsilyl azide (13.5 ml) was heated to 100° C. for 24 h. The cooled mixture was cautiously decomposed with methanol (50 ml) and evaporated in vacuo to give the title compound (5.7 g) as a white solid.

Workup

  1. customevaporated in vacuo

Sources & evidence

ORD record
ord-17cd3a618aeb453abdda756edd026a5b
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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