Ethyl propiolate → Ethyl 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-2-carboxylate

HRID 2307252Notes

Reaction equation

HRID 2307252 reaction equation
[N:1]1O[C:3]([O-])=[C:4]2[CH2:9][CH2:8][CH2:7][CH2:6][N+:5]=12.[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[C:12]#C>C1(C)C(C)=CC=CC=1>[N:1]1[N:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]2=[CH:3][C:12]=1[C:11]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 12182Ethyl propiolateHCID 118450904,5,6,7-Tetrahydro-(1,2,3)oxadiazolo(3,4-a)pyridin-8-ium-3-olate

Product 1

HCID 11845784Ethyl 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 4,5,6,7-tetrahydro[1,2,3]oxadiazolo[3,4-a]pyridin-8-ium-3-olate (Heterocycles; 1990; 31; 481), (13.0 g, 93 mmol), and ethyl propiolate (28.5 ml, 278 mmol), in xylene (250 ml) was heated under reflux for 2 hours. The cooled mixture was evaporated under reduced pressure. The residual oil was purified by column chromatography on silica gel using ether as the eluant, to afford the title compound as an oil, 5.82 g.

Workup

  1. temperatureunder reflux for 2 hours
  2. customThe cooled mixture was evaporated under reduced pressure
  3. customThe residual oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-19fbf650ee5f4366b4dd40ced2f44c0a
Source dataset
uspto-grants-2004_12
Patent number
US06831074B2

Reaction notes

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