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

HRID 359382

반응식

HRID 359382 반응식
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=O)=[CH:2]1.[CH3:8][C:9]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13](=[O:14])[CH:12]=[C:11]([CH3:15])[O:10]1.[OH-].[Na+].[Cl-].[Na+]>C(O)C>[CH3:8][C:9]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13](=[O:14])[CH:12]=[C:11]([CH:15]=[CH:6][C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)[O:10]1

참가 물질

6

반응물 4

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 681353-ThiophenecarboxaldehydeHCID 150866992,5-dimethyl-2-phenyl-3(2H)-furanone

생성물 1

HCID 543182742-Methyl-2-phenyl-5-[2-(3-thienyl)ethenyl]-3(2H)-furanone수율 71.1%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 3-thiophenecarboxaldehyde (1.07 g, 9.6 mM) and 2,5-dimethyl-2-phenyl-3(2H)-furanone (1.5 g, 8 mM) in ethanol (50 mL), was added 1N aqueous sodium hydroxide (1.6 mL, 1.6 mM). After the reaction solution was stirred at room temperature for one day, saturated aqueous sodium chloride (400 mL) was added. The aqueous layer was extracted with dichloromethane (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 yellow liquid. The liquid was purified by chromatography (silica gel, pet. ether-ethyl acetate) to afford a yellow solid (1.6 g, 71% yield), m.p. 75°-77° C.

후처리

  1. extractionThe aqueous layer was extracted with dichloromethane (3×100 mL)
  2. washThe combined dichloromethane extracts were washed with saturated aqueous sodium chloride (50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a yellow liquid
  7. customThe liquid was purified by chromatography (silica gel, pet. ether-ethyl acetate)

출처 및 근거

ORD 기록
ord-a78c709543a540b3a961308bb590019e
출처 데이터셋
uspto-grants-1991_03
특허 번호
US05001126

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