Tetrahydrofuran → 1-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-2-[1-(4-fluorophenyl)-2-methylsulfonylethylidene]-1-methylhydrazine

HRID 579251ノート

反応式

HRID 579251 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:14][NH:15][CH3:16])[CH2:9][S:10]([CH3:13])(=[O:12])=[O:11])=[CH:4][CH:3]=1.O1CCCC1.C(N(CC)CC)C.[CH2:29]([C:31]1[CH:36]=[C:35]([CH3:37])[CH:34]=[C:33]([CH2:38][CH3:39])[C:32]=1[C:40](=[O:44])[C:41](Cl)=[O:42])[CH3:30]>O>[CH2:29]([C:31]1[CH:36]=[C:35]([CH3:37])[CH:34]=[C:33]([CH2:38][CH3:39])[C:32]=1[C:40](=[O:44])[C:41]([N:15]([CH3:16])[N:14]=[C:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[CH2:9][S:10]([CH3:13])(=[O:12])=[O:11])=[O:42])[CH3:30]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 569427122-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl chlorideHCID 866893531-[1-(4-Fluorophenyl)-2-methylsulfonylethylidene]-2-methylhydrazine

生成物 1

HCID 866893541-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-2-[1-(4-fluorophenyl)-2-methylsulfonylethylidene]-1-methylhydrazine収率 60.8%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a 30 ml volume two-necked flask, 1-[1-(4-fluorophenyl)-2-methylsulfonylethylidene]-2-methylhydrazine (5-2-4) (0.90 g) and anhydrous tetrahydrofuran (5 ml) were added under a nitrogen atmosphere, and added triethylamine (0.37 g) under cooling. To the mixture, 2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl chloride (6-a) (0.88 g) was added dropwise below 0° C., and stirred under ice-cooling for 2 hours. The reaction mixture was added to water, and extracted with tert-butyl methyl ether. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (tert-butyl methyl ether) to give 1.0 g of 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-2-[1-(4-fluorophenyl)-2-methylsulfonylethylidene]-1-methylhydrazine ((4-64)-(1)-39).

後処理

  1. temperatureunder cooling
  2. temperaturecooling for 2 hours
  3. extractionextracted with tert-butyl methyl ether
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (tert-butyl methyl ether)

出典と根拠

ORDレコード
ord-6e304951b9a4493f85884c43428797c7
出典データセット
uspto-grants-2015_05
特許番号
US09040709B2

反応ノート

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