Hydrochloric Acid → 1-[(3-Acetyl-4-hydroxyphenyl)methyl]-2-pyrrolidinone

HRID 1781403Notes

Reaction equation

HRID 1781403 reaction equation
[H-].[Na+].[NH:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8].Cl[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([OH:20])=[C:15]([C:17](=[O:19])[CH3:18])[CH:16]=1.Cl>CN(C)C=O>[C:17]([C:15]1[CH:16]=[C:11]([CH2:10][N:3]2[CH2:7][CH2:6][CH2:5][C:4]2=[O:8])[CH:12]=[CH:13][C:14]=1[OH:20])(=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 22557013HCID 22557013, compound

Product 1

HCID 190454421-[(3-Acetyl-4-hydroxyphenyl)methyl]-2-pyrrolidinoneYield 82.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of sodium hydride (60% dispersion in mineral oil, 0.80 g, 20.0 mmol) in 15 mL dry dimethylformamide under argon, cooled in an ice-bath was added dropwise a solution of 2-pyrrolidinone (1.70 g, 20.0 mmol) in 5 mL dimethylformamide. The ice-bath was removed, the mixture was stirred 30 minutes, and a solution of 5'-(chloromethyl)-2'-hydroxyacetophenone (1.85 g, 10.0 mmol) in 5 mL dimethylformamide was added dropwise. The mixture was stirred four hours, poured into 75 mL ice water, acidified with 7 mL 3N hydrochloric acid, and extracted with methylene chloride (3×75 mL). The extract was washed with water (25 mL) and brine, dried over Na2SO4, and filtered. The filtrate was concentrated in vacuo to give crude product which was purified by flash chromatography on silica gel slutlug with 2:98 methanol:chloroform to give 1.92 g (82%) product as a viscous oil.

Workup

  1. temperaturecooled in an ice-bath
  2. customThe ice-bath was removed
  3. stirringThe mixture was stirred four hours
  4. extractionextracted with methylene chloride (3×75 mL)
  5. washThe extract was washed with water (25 mL) and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. customto give crude product which
  10. customwas purified by flash chromatography on silica gel slutlug with 2:98 methanol

Sources & evidence

ORD record
ord-08e1b55496fe4cbebd59e0dd24ef1b14
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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