Phenyl formate → 5-((1H-Pyrrol-2-YL)methyl)-1H-pyrrole-2-carbaldehyde

HRID 2425462

Reaction equation

HRID 2425462 reaction equation
[CH:1]1[CH:5]=[C:4]([CH2:6][C:7]2[NH:11][CH:10]=[CH:9][CH:8]=2)[NH:3][CH:2]=1.C1([Mg]Br)C(C)=CC(C)=CC=1C.[CH:23](OC1C=CC=CC=1)=[O:24]>C1C2=CC3NC(C=C4N=C(C=C5NC(=CC(=N2)C1)C=C5)C=C4)=CC=3.C1COCC1>[CH:9]1[CH:8]=[C:7]([CH2:6][C:4]2[NH:3][C:2]([CH:23]=[O:24])=[CH:1][CH:5]=2)[NH:11][CH:10]=1

Participants

6

Reactant 3

HCID 74626Phenyl formateHCID 140814DipyrromethaneHCID 178425415HCID 178425415, compound

Product 1

HCID 167326915-((1H-Pyrrol-2-YL)methyl)-1H-pyrrole-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 65106ChlorinSolvent

Procedure

As part of our work in chlorin chemistry, we recently developed an efficient route for the synthesis of 1-formyldipyrromethanes.21 The formylation method entailed traditional Vilsmeier formylation or treatment of a solution of dipyrromethane in THF at room temperature with 2 molar equiv of MesMgBr and then at −78° C. with 2 molar equiv of phenyl formate. The subsequent workup and column chromatography afforded the desired 1-formyldipyrromethane in good yields.

Workup

  1. customfor the synthesis of 1-formyldipyrromethanes.21 The formylation method
  2. customat room temperature
  3. customat −78° C.

Sources & evidence

ORD record
ord-8981bbf13a2a446daccc74351713951b
Source dataset
uspto-grants-2011_06
Patent number
US07964720B2

Linked notes

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