Water → HCID 86747465, 화합물

HRID 1197637노트

반응식

HRID 1197637 반응식
[CH2:1]1[CH2:5][O:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:8][CH:9]([CH3:28])[C:10](=[C:13]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[CH:11]=O.[OH2:29]>>[CH3:8][CH:9]([CH3:28])[C:10](=[C:13]([C:14]1[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=1)[C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)/[CH:11]=[CH:2]/[C:3]([O:4][CH2:5][CH3:1])=[O:29]

참가 물질

5

반응물 4

HCID 962WaterHCID 8028Tetrahydrofuran2회HCID 24758Sodium hydrideHCID 140335263-Methyl-2-bis(4-fluorophenyl)methylidenbutanal

생성물 1

HCID 86747465HCID 86747465, 화합물수율 79%

실험 절차

A THF (2.0 ml) solution of triethyl phosphonoacetate (EtO)2P(O)CH2COOEt (0.224 g, 0.198 ml, 1.00 mmol) was added at 0° C. under argon atmosphere to sodium hydride (content 60%, oil dispersion, 42 mg, 1.04 mmol) which had been washed with hexane, and the mixture was stirred for 30 minutes. To the mixture was added a THF (1 ml) solution of 3-methyl-2-bis(4-fluorophenyl)methylidenbutanal (0.286 g, 1.0 mmol) prepared according to the method described in Tetrahedron Lett., 29, 929 (1988). After stirring at room temperature overnight, the mixture was then diluted with water (25 ml) and extracted with hexane (30 ml×3 times). The organic layer was washed with water (30 ml×twice) and saturated sodium chloride aq solution and finally dried over anhydrous magnesium sulfate. Concentration in vacuo followed by purification by thin layer chromatography (silica gel, ethyl acetate:hexane=1:9) to give 0.28 g (79% yield) of ethyl (E)-5-methyl-4-bis(4-fluorophenyl)methylidene-2-hexenoate.

후처리

  1. washhad been washed with hexane
  2. customprepared
  3. stirringAfter stirring at room temperature overnight
  4. extractionextracted with hexane (30 ml×3 times)
  5. washThe organic layer was washed with water (30 ml×twice) and saturated sodium chloride aq solution
  6. dry with materialfinally dried over anhydrous magnesium sulfate
  7. concentrationConcentration in vacuo
  8. customfollowed by purification by thin layer chromatography (silica gel, ethyl acetate:hexane=1:9)

출처 및 근거

ORD 기록
ord-508dc88538d3428283d03e371538da45
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05276154

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