Water → HCID 69020769, compound

HRID 1865079Notes

Reaction equation

HRID 1865079 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:9]([O:11][C:12]([C:14]1[N:15]([CH3:31])[C:16]([CH2:29][CH3:30])=[C:17]([C:27]#[N:28])[C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([CH:25]=[O:26])=[CH:21][CH:20]=1)=[O:13])[CH3:10].O>C1COCC1>[CH2:9]([O:11][C:12]([C:14]1[N:15]([CH3:31])[C:16]([CH2:29][CH3:30])=[C:17]([C:27]#[N:28])[C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([CH:25]([OH:26])[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:21][CH:20]=1)=[O:13])[CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 86611444HCID 86611444, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 69020769HCID 69020769, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Add phenyl magnesium bromide (192 uL, 0.58 mmol) to 4-cyano-5-ethyl-3-(4-formyl-phenyl)-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester [(0.020 g, 0.64 mmol, prepared in example E-152] in THF with stirring at −78° C. After 30 minutes, gradually allow the reaction mixture to warm to ambient temperature. After 2 hours, pour the reaction mixture into water and extract with EtOAc. Combine the organic extracts, wash with water and brine, dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Purify the residue by flash chromatography eluting with ethyl acetate:hexanes to provide the title compound. Mass spectrum (m/e): 406.1 (M+18).

Workup

  1. temperatureto warm to ambient temperature
  2. waitAfter 2 hours
  3. extractionextract with EtOAc
  4. washwash with water and brine
  5. dry with materialdry over anhydrous magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure
  8. customPurify the residue by flash chromatography
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-d69cb44178f745b3ba36b3d26c090164
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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