Water → HCID 10107997、化合物

HRID 1096486ノート

反応式

HRID 1096486 の反応式
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([CH:10]=[O:11])[C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CN(C=O)C.CCOC(C)=O>[C:14]1([S:20]([N:1]2[C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([CH:10]=[O:11])[C:4]=3[CH:3]=[CH:2]2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

7

反応物 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 333703Indole-4-carboxaldehyde

生成物 1

HCID 10107997HCID 10107997、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

1H-Indole-4-carbaldehyde (24.8 g, 0.17 mol) was dissolved in dry DMF (500 ml), cooled in ice-bath and NaH (7.5 g (60% suspension in oil), 0.19 mol, 1.1 eq.) was added. After stirring for a few minutes, the cold bath was removed and the r×n mixture was stirred at room temperature for 40 min. under Ar. The insoluble NaH clumps were brought in solution by means of sonication for a few minutes. The mixture was cooled in ice-bath and benzenesulfonyl chloride (23.9 ml, 0.188 mol, 1.1 e.q.) was added dropwise over 3 min. The reaction mixture was stirred at room temperature for 1 hour, then poured slowly into a mixture of water (1 L) and EtOAc (200 ml). The aqueous phase was extracted with EtOAc (5×100 ml), the organic phase was washed with brine (200 ml), dried over Na2SO4 and evaporated. The residue was purified on silica flash column using petroleum ether/EtOAc (1:1) giving the product as a colorless crystalline solid. Yield: 45.5 g. MS m/z 286 [M+H]+.

後処理

  1. temperaturecooled in ice-bath
  2. customthe cold bath was removed
  3. stirringthe r×n mixture was stirred at room temperature for 40 min. under Ar
  4. customThe insoluble NaH clumps were brought in solution by means of sonication for a few minutes
  5. temperatureThe mixture was cooled in ice-bath
  6. stirringThe reaction mixture was stirred at room temperature for 1 hour
  7. extractionThe aqueous phase was extracted with EtOAc (5×100 ml)
  8. washthe organic phase was washed with brine (200 ml)
  9. dry with materialdried over Na2SO4
  10. customevaporated
  11. customThe residue was purified on silica flash column

出典と根拠

ORDレコード
ord-6b8ac0f6da8d46f79250e4ac216cffbd
出典データセット
uspto-grants-2012_03
特許番号
US08138333B2

反応ノート

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