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Water → Benzyl 3-formyl-1H-indole-1-carboxylate

HRID 1249232
ノート
印刷プレビュー

反応式

HRID 1249232 の反応式
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]=[O:13])=[CH:4]1.Cl[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].O>C1COCC1>[C:15]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]=[O:13])=[CH:4]1)([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 10256Indole-3-CarboxaldehydeHCID 10387Benzyl chloroformateHCID 24758Sodium hydride

生成物 1

HCID 13711097Benzyl 3-formyl-1H-indole-1-carboxylate収率 88%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

Sodium hydride (1.99 g, 50% in oil, 41.4 mmol, extracted with hexanes) was stirred in THF (50 ml) in a flame-dried flask at 0° C. under nitrogen. Indole-3-carboxaldehyde (5.00 g, 34.5 mmol) was added as a powder in small portions, and then the mixture was warmed to 40° C. for 30 min. The mixture was again cooled to 0° C., and benzyl chloroformate (4.92 ml, 34.5 mmol) was added. After warming to room temperature and stirring overnight, the mixture was poured into water (50 ml) and extracted with CH2Cl2 (50 ml). The organic layer was washed with water (50 ml), dried with MgSO4, filtered and evaporated to 9.2 g (95%) of a gold-brown oil. Crystallization from hot hexane gave 8.47 g (88%) of white crystalline product: mp 70°-71°

後処理

  1. temperatureThe mixture was again cooled to 0° C.
  2. temperatureAfter warming to room temperature
  3. extractionextracted with CH2Cl2 (50 ml)
  4. washThe organic layer was washed with water (50 ml)
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customevaporated to 9.2 g (95%) of a gold-brown oil
  8. customCrystallization from hot hexane

出典と根拠

ORDレコード
ord-c5f5c7f62e084d32b44e8b1dc6485aaf
出典データセット
uspto-grants-1986_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04629794

反応ノート

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