Water → HCID 67136311、化合物

HRID 230888

反応式

HRID 230888 の反応式
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[C:13]([CH:20]=O)=[CH:14][NH:15]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O>CS(C)=O.[Cl-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1>[CH2:3]([O:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[C:13](/[CH:20]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH:14][NH:15]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

参加物

6

反応物 3

HCID 962WaterHCID 24758Sodium hydrideHCID 70158464-(benzyloxy)-1H-indole-3-carbaldehyde

生成物 1

HCID 67136311HCID 67136311、化合物収率 197.7%

試薬・触媒・溶媒 2

HCID 70671Benzyltriphenylphosphonium chloride触媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
65 °C

実験手順

To a suspension of sodium hydride (60%, 48 mg) in dimethyl sulfoxide (3 mL) was added benzyltriphenylphosphonium chloride (0.47 g), and the mixture was stirred at 65° C. for 1 hour. The reaction mixture was cooled in ice. To the mixture was added 4-benzyloxy-3-formylindole (0.25 g), and the mixture was stirred at 85° C. for 3 hours. The reaction mixture was cooled to room temperature. To the mixture was added water, and the mixture was extracted with ethyl acetate (three times). The extract was washed with water twice, a saturated aqueous sodium hydrogen carbonate solution and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on aminopropylated silica gel (eluent: n-hexane/ethyl acetate=3/1) to give the title compound (0.32 g).

後処理

  1. temperatureThe reaction mixture was cooled in ice
  2. stirringthe mixture was stirred at 85° C. for 3 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. extractionthe mixture was extracted with ethyl acetate (three times)
  5. washThe extract was washed with water twice
  6. dry with materiala saturated aqueous sodium hydrogen carbonate solution and brine successively, and dried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by column chromatography on aminopropylated silica gel (eluent: n-hexane/ethyl acetate=3/1)

出典と根拠

ORDレコード
ord-a4df83a8600b4fe4971416a94b0c505e
出典データセット
uspto-grants-2009_07
特許番号
US07566699B2

関連ノート

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