Isobutylene → HCID 24786837, compound

HRID 2375796Notes

Reaction equation

HRID 2375796 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[NH:12][C:13]([CH:16]=[O:17])=[CH:14][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P([O-])(O)(O)=[O:19].[Na+].Cl([O-])=O.[Na+].C=C(C)C>C(O)CCC.O>[CH2:1]([O:8][C:9]([C:11]1[NH:12][C:13]([C:16]([OH:19])=[O:17])=[CH:14][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8255IsobutyleneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 71349636Benzyl 5-formyl-1H-pyrrole-2-carboxylate

Product 1

HCID 24786837HCID 24786837, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Procedure

To a solution of 5-formyl-1H-pyrrole-2-carboxylic acid benzyl ester (8.0 g) in n-butanol (300 mL) and water (112 mL) was added sodium dihydrogen phosphate (6.28 g), sodium chlorite (9.47 g) and isobutene (58g). The mixture was stirred for 20 h at RT after which it was concentrated. After purification of the residue by flash column chromatography on silica (DCM/MeOH 15:1 to 1:1) 10.0 g of 1H-pyrrole-2,5-dicarboxylic acid monobenzyl ester were obtained.

Workup

  1. concentrationwas concentrated
  2. customAfter purification of the residue by flash column chromatography on silica (DCM/MeOH 15:1 to 1:1) 10.0 g of 1H-pyrrole-2,5-dicarboxylic acid monobenzyl ester
  3. customwere obtained

Sources & evidence

ORD record
ord-bf9f22643c92426a96a196d51c048f84
Source dataset
uspto-grants-2008_12
Patent number
US07465806B2

Reaction notes

Loading…