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

HRID 1173427ノート

反応式

HRID 1173427 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 7855861-(4-hydroxyphenyl)pyrrolidin-2-one収率 19.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-a1bc74e7e76648dbaa7da23bb8203476
出典データセット
uspto-grants-2010_11
特許番号
US07834063B2

反応ノート

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