Acetone → HCID 58674658, compound

HRID 1994118Notes

Reaction equation

HRID 1994118 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]2[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]2[CH3:14])[CH:5]=[CH:6][CH:7]=1.[Li]CCCC.[CH3:20][C:21]([CH3:23])=[O:22]>C1COCC1>[CH3:14][C:9]1[N:8]([C:4]2[CH:3]=[C:2]([C:21]([OH:22])([CH3:23])[CH3:20])[CH:7]=[CH:6][CH:5]=2)[C:12]([CH3:13])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 47636541-(3-bromophenyl)-2,5-dimethyl-1H-pyrroleHCID 178418339Butyllithium

Product 1

HCID 58674658HCID 58674658, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(3-bromophenyl)-2,5-dimethyl-1H-pyrrole (1.50 g, 6.00 mmol) in THF (25 mL) was cooled to −78° C. under an atmosphere of argon. To this solution was added n-BuLi (2.50 M in hexane, 2.76 mL, 6.90 mmol) dropwise via syringe. After 30 min, acetone (0.572 mL, 7.8 mmol) was added to the cold solution dropwise via syringe. After 10 min, the cold bath was removed and the reaction mixture was allowed to warm to rt. After 5.5 h, the reaction was quenched by the addition of water. The mixture was extracted with EtOAc and the organic solutions dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography to give the desired product (0.84 g, 61%). LCMS: (FA) ES+ 230.1 (M+1).

Workup

  1. waitAfter 10 min
  2. customthe cold bath was removed
  3. waitAfter 5.5 h
  4. customthe reaction was quenched by the addition of water
  5. extractionThe mixture was extracted with EtOAc
  6. dry with materialthe organic solutions dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8bd329db5afa40d19095c0ad02d41faf
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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