Benzyl 2-(triphenyl-lambda5-phosphanylidene)acetate → methyl 3-[2-((E)-2-benzyloxycarbonylethenyl)pyrrol-1-yl)benzoate

HRID 399830Notes

Reaction equation

HRID 399830 reaction equation
[CH:1]([C:3]1[N:4]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][CH:7]=1)=O.C1(P(=[CH:37][C:38]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:39])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH2:41]([O:40][C:38](/[CH:37]=[CH:1]/[C:3]1[N:4]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][CH:7]=1)=[O:39])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

4

Reactant 2

HCID 3862746Benzyl 2-(triphenyl-lambda5-phosphanylidene)acetateHCID 17604923methyl 3-(2-formyl-1H-pyrrol-1-yl)benzoate

Product 1

HCID 18945360methyl 3-[2-((E)-2-benzyloxycarbonylethenyl)pyrrol-1-yl)benzoateYield 48.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The solution of methyl 3-(2-formylpyrrol-1-yl)benzoate (1.0 g) and benzyl (triphenylphosphoranylidene)acetate (1.8 g) in tetrahydrofuran (10 ml) were heated under reflux for 30 hours. After evaporating the solvent, the residue was purified by column chromatography on silica gel eluting with toluene. The fractions containing the desired product were collected and evaporated in vacuo to give methyl 3-[2-((E)-2-benzyloxycarbonylethenyl)pyrrol-1-yl)benzoate (0.77 g) as an oil.

Workup

  1. temperatureunder reflux for 30 hours
  2. customAfter evaporating the solvent
  3. customthe residue was purified by column chromatography on silica gel eluting with toluene
  4. additionThe fractions containing the desired product
  5. customwere collected
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-55b1b86ed9a242dda54409e1d051e08f
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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