1-benzyl-1H-pyrrole-2-carbaldehyde → HCID 68593500, compound

HRID 748072Notes

Reaction equation

HRID 748072 reaction equation
[CH2:1]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH:13]=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:15]([Mg]Br)([CH3:17])[CH3:16]>C1COCC1>[CH2:1]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH:13]([OH:14])[CH:15]([CH3:17])[CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 111269641-benzyl-1H-pyrrole-2-carbaldehydeHCID 178418365HCID 178418365, compound

Product 1

HCID 68593500HCID 68593500, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1-benzyl-1H-pyrrole-2-carbaldehyde (0.50 g, 2.7 mmol) in THF (20 mL) at 0° C. was added a solution of i-PrMgBr (5.4 mL, 1N in THF, 5.4 mmol). The reaction mixture was warmed to room temperature and after 1.5 h it was quenched with saturated aqueous ammonium chloride, extracted with EtOAc, dried (Na2SO4) and concentrated. Column chromatography (EtOAc/hexanes, 1:4) provided 0.345 g (56%) of 1-(1-benzyl-1H-pyrrol-2-yl)-2-methylpropan-1-ol as an oil.

Workup

  1. customwas quenched with saturated aqueous ammonium chloride
  2. extractionextracted with EtOAc
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8783486082344aa09ca65b33ff87acb1
Source dataset
uspto-grants-2008_07
Patent number
US07399778B2

Reaction notes

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