Sodium Chloride → 2-Methyl-2-phenyl-5-[2-(4-pyridinyl)ethenyl]-3(2H)-furanone

HRID 1089517

反応式

HRID 1089517 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[CH3:9][C:10]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14](=[O:15])[CH:13]=[C:12]([CH3:16])[O:11]1.N12CCCN=C1CCCCC2.[Cl-].[Na+]>C(O)C>[CH3:9][C:10]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14](=[O:15])[CH:13]=[C:12]([CH:16]=[CH:7][C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)[O:11]1

参加物

6

反応物 4

HCID 5234Sodium ChlorideHCID 133894-PyridinecarboxaldehydeHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 150866992,5-dimethyl-2-phenyl-3(2H)-furanone

生成物 1

HCID 543671172-Methyl-2-phenyl-5-[2-(4-pyridinyl)ethenyl]-3(2H)-furanone収率 37%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
60 °C

実験手順

To a solution of 4-pyridinecarboxaldehyde (1.4 mL, 14.9 mM) and 2,5-dimethyl-2-phenyl-3(2H)-furanone (2.0 g, 10.6 mM) in ethanol (50 mL), was added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 323 mg, 2.1 mM). The reaction solution was heated at 60° C. for 4 hours. After the reaction solution cooled to room temperature, saturated aqueous sodium chloride (400 mL) was added. The aqueous layer was extracted with diethyl ether (3×100 mL). The combined dichloromethane extracts were washed with saturated aqueous sodium chloride (50 mL), dried over MgSO4, filtered and concentrated to give a red gummy product. The crude product was purified by chromatography (silica gel, pet. ether-ethyl acetate) to give a white crystalline solid (1.1 g, 37% yield), m.p. 165°-166° C.

後処理

  1. temperatureAfter the reaction solution cooled to room temperature
  2. extractionThe aqueous layer was extracted with diethyl ether (3×100 mL)
  3. washThe combined dichloromethane extracts were washed with saturated aqueous sodium chloride (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a red gummy product
  8. customThe crude product was purified by chromatography (silica gel, pet. ether-ethyl acetate)

出典と根拠

ORDレコード
ord-df3edf00e4b94ea6b1e562c45bf0c166
出典データセット
uspto-grants-1990_10
特許番号
US04966905

関連ノート

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