Sodium Chloride → 2-Phenyl-2-methyl-5-[2-(3-pyridinyl)ethenyl]-3(2H)-furanone

HRID 1085583

反応式

HRID 1085583 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[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.[OH-].[Na+].[Cl-].[Na+]>C(O)C>[C:17]1([C:10]2([CH3:9])[C:14](=[O:15])[CH:13]=[C:12]([CH:16]=[CH:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[O:11]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

参加物

6

反応物 4

HCID 5234Sodium ChlorideHCID 103713-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 150866992,5-dimethyl-2-phenyl-3(2H)-furanone

生成物 1

HCID 541857672-Phenyl-2-methyl-5-[2-(3-pyridinyl)ethenyl]-3(2H)-furanone収率 54.3%

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 3-pyridinecarboxaldehyde (1.03 g, 9.6 mM) and 2,5-dimethyl-2-phenyl-3(2H)-furanone (1.0 g, 8 mM) in ethanol (50 mL), was added 1N aqueous sodium hydroxide (2.4 mL, 2.4 mM). The reaction solution was heated at 60° C. for 8 hours. After the reaction solution cooled to room temperature, saturated aqueous sodium chloride (200 mL) was added. The aqueous layer was extracted with diethyl ether (3×100 mL). The combined ethereal extracts were washed with saturated aqueous sodium chloride (50 mL), dried over MgSO4, filtered and concentrated to give a brown solid. The crude product was purified by chromatography (silica gel, pet. ether-ethyl acetate) to afford a yellow crystalline solid (0.8 g, 36.3% yield), m.p. 106°-108° 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 ethereal extracts were washed with saturated aqueous sodium chloride (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a brown solid
  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-85ab62e24ea14702b94e6f7291dee02b
出典データセット
uspto-grants-1991_04
特許番号
US05010102

関連ノート

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