Ethyl propiolate → HCID 11845245, compound

HRID 1158890Notes

Reaction equation

HRID 1158890 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[C:2]#[CH:3].[N+:8]([C:11]1[CH:30]=[CH:29][C:14]([CH2:15][O:16][C:17]([N:19]2[CH2:27][CH2:26][N+:25]3[C-:21](C(=O)O[N:24]=3)[CH2:20]2)=[O:18])=[CH:13][CH:12]=1)([O-:10])=[O:9]>CC1C=CC=CC=1C>[N+:8]([C:11]1[CH:12]=[CH:13][C:14]([CH2:15][O:16][C:17]([N:19]2[CH2:27][CH2:26][N:25]3[N:24]=[C:2]([C:1]([O:5][CH2:6][CH3:7])=[O:4])[CH:3]=[C:21]3[CH2:20]2)=[O:18])=[CH:29][CH:30]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 12182Ethyl propiolateHCID 178525195HCID 178525195, compound

Product 1

HCID 11845245HCID 11845245, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Ethyl propiolate (cont. 99%) (8.28 g) was added to the o-xylene (348 mL) solution of 5-(4-nitrobenzyloxycarbonyl)-3-oxo-3a,4,6,7-tetrahydro-3H-2-oxa-1,5-diaza-7a-azoniainden-3a-ide (22.3 g) under a nitrogen atmosphere and refluxed for 16 h. The solution was concentrated under reduced pressure, followed by silica-gel column chromatography 3 times (n-hexane/AcOEt=2/1-1/3). The titled compound was obtained as pale yellow crystals (16.78 g, 64%). Besides, 6,7-dihydro-4H-pyrazolo[1,5-a]pyrazine-3,5-dicarboxylic acid 3-ethyl ester 5-(4-nitrobenzyl) ester was obtained as pale yellow crystals (6.18 g, 24%).

Workup

  1. temperaturerefluxed for 16 h
  2. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-43aa327daa004dfea62a7ea2731d7c00
Source dataset
uspto-grants-2010_10
Patent number
US07812014B2

Reaction notes

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