Water → HCID 66991975, compound

HRID 556731Notes

Reaction equation

HRID 556731 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH:15]=O)([O-:3])=[O:2].C(P(CCCC)(CCCC)[CH2:22][CH:23]1[O:27][CH2:26][CH2:25][O:24]1)CCC.CC([O-])(C)C.[K+].O>CS(C)=O>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH:15]=[CH:22][CH:23]1[O:27][CH2:26][CH2:25][O:24]1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 47153911-(2-nitrophenyl)-1H-pyrrole-2-carbaldehydeHCID 23665647Potassium tert-butoxideHCID 178454894HCID 178454894, compound

Product 1

HCID 66991975HCID 66991975, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2.98 g (13.8 mmol) 2a, 1.2 eqv. of tributyl-[1,3]dioxolan-2-ylmethyl-λ5-phosphane and 1.5 eqv. KOtBu in DMSO was stirred at 60° C. for 24 hours. The reaction was monitored by TLC (EtOAc:petroleum ether 1:2). After cooling, the reaction mixture was poured into water and extracted with ether and the solvent was evaporated. The semi-solid residue was diluted with ether and filtrated to remove residual Bu3PO and the product was purified by column chromatography (EtOAc: petroleum ether 1:2) to yield 2.6 g (66%) of 3a.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ether
  3. customthe solvent was evaporated
  4. additionThe semi-solid residue was diluted with ether
  5. filtrationfiltrated
  6. customto remove residual Bu3PO
  7. customthe product was purified by column chromatography (EtOAc: petroleum ether 1:2)

Sources & evidence

ORD record
ord-03fb3124c56c4ec49c49daa9231fafe0
Source dataset
uspto-grants-2011_11
Patent number
US08058306B2

Reaction notes

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