Water → HCID 86747465、化合物

HRID 1197637ノート

反応式

HRID 1197637 の反応式
[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]

参加物

5

反応物 4

HCID 962WaterHCID 8028Tetrahydrofuran2 回HCID 24758Sodium hydrideHCID 140335263-Methyl-2-bis(4-fluorophenyl)methylidenbutanal

生成物 1

HCID 86747465HCID 86747465、化合物収率 79%

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-508dc88538d3428283d03e371538da45
出典データセット
uspto-grants-1994_01
特許番号
US05276154

反応ノート

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