4-Aminophenol → 1-(4-hydroxyphenyl)pyrrolidin-2-one

HRID 1173427노트

반응식

HRID 1173427 반응식
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([OH:8])[CH:2]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:16][CH2:17][CH2:18][C:19](Cl)=[O:20].CN(C=O)C>CC#N.O>[OH:8][C:3]1[CH:4]=[CH:5][C:6]([N:7]2[CH2:16][CH2:17][CH2:18][C:19]2=[O:20])=[CH:1][CH:2]=1

참가 물질

7

반응물 4

HCID 4034-AminophenolHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 783704-Chlorobutyryl chloride

생성물 1

HCID 7855861-(4-hydroxyphenyl)pyrrolidin-2-one수율 19.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

To a solution of p-aminophenol (0.545 g, 5.00 mmol) in dry MeCN (5 mL) at 0° C. was added K2CO3 (1.38 g, 10.0 mmol), followed by dropwise addition of 4-chlorobutanoyl chloride (0.56 mL, 5.0 mmol). The mixture was stirred at rt for 40 min and then brought to reflux. Dry DMF (5 mL) was added after 90 min and heating was continued for an additional 2 h. The mixture was cooled, poured into water, and extracted with EtOAc (×8). Combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording 0.171 g of the title compound as a colorless solid: MS (APCI) m/z 177 (M+).

후처리

  1. temperatureto reflux
  2. temperatureheating
  3. waitwas continued for an additional 2 h
  4. temperatureThe mixture was cooled
  5. extractionextracted with EtOAc (×8)
  6. washCombined organics were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash chromatography (EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-a1bc74e7e76648dbaa7da23bb8203476
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834063B2

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