Benzyl Alcohol → 4-Benzyloxy-3-pyrrolin-2-one

HRID 1722471ノート

反応式

HRID 1722471 の反応式
[CH3:1][O:2][C:3]1[CH2:7][NH:6][C:5](=[O:8])[CH:4]=1.C(O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CS(O)(=O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([O:2][C:3]1[CH2:7][NH:6][C:5](=[O:8])[CH:4]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

6

反応物 4

HCID 244Benzyl AlcoholHCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 5747694-methoxy-2,5-dihydro-1H-pyrrol-2-one

生成物 1

HCID 27247414-Benzyloxy-3-pyrrolin-2-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

5.7 g (50 mmol) of 4-methoxy-3-pyrrolin-2-one and 10.8 g (100 mmol) of benzyl alcohol were mixed with 0.4 g (4 mmol) of methanesulfonic acid and stirred for 24 hours at 80° C. and 20 mbars. Then the reaction solution was mixed with 50 ml of ice water and 100 ml of methylene chloride, and neutralized with 4 ml of saturated NaHCO3 solution. The aqueous phase was extracted twice with 50 ml of methylene chloride each. After drying of the organic phase over Na2SO4 and distilling off of the solvent, the residue was mixed with 150 ml of ice water, heated to 100° C. and azeotropically distilled off with 100 ml of water-benzyl alcohol. The crystals precipitated during cooling were recrystallized hot from 50 ml of toluene. 6.7 g of white, crystalline product with a melting point of 147° to 148° C. was obtained:

後処理

  1. extractionThe aqueous phase was extracted twice with 50 ml of methylene chloride each
  2. dry with materialAfter drying of the organic phase over Na2SO4
  3. distillationdistilling off of the solvent
  4. additionthe residue was mixed with 150 ml of ice water
  5. temperatureheated to 100° C.
  6. distillationazeotropically distilled off with 100 ml of water-benzyl alcohol
  7. customThe crystals precipitated
  8. temperatureduring cooling
  9. customwere recrystallized hot from 50 ml of toluene
  10. custom6.7 g of white, crystalline product with a melting point of 147° to 148° C. was obtained

出典と根拠

ORDレコード
ord-04e440d11a534283a9a851cb36ad1d00
出典データセット
uspto-grants-1989_08
特許番号
US04855451

反応ノート

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