1-(Phenylsulfonyl)-3-indolecarboxaldehyde → [1-(Phenylsulfonyl)-1H-Indol-3-Yl]Methanol

HRID 254188

반응식

HRID 254188 반응식
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([CH:19]=[O:20])=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>ClCCl>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([CH2:19][OH:20])=[CH:11]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

4

반응물 2

HCID 3633341-(Phenylsulfonyl)-3-indolecarboxaldehydeHCID 4311764Sodium borohydride

생성물 1

HCID 2776213[1-(Phenylsulfonyl)-1H-Indol-3-Yl]Methanol

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In a three necked round bottom flask equipped with pressure equalizing funnel, 1-Benzenesulfonyl-1H-indole-3-carboxaldehyde (D1, 2.86 g, 0.01 mole) and dichloromethane (8 mL) were taken. Sodiumborohydride (0.005-0.01 mole) was added slowly at room temperature and the reaction mixture was stirred well for next 3-4 hours. After the completion of reaction (TLC, 3-5 hours), the product was isolated by distillation under reduced pressure. The residue was extracted with ethyl acetate (2×25 mL). The combined organic extracts were washed with water, followed by brine, dried over anhydrous sodium sulfate. The organic layer was evaporated under vacuum. The residue was generally an oily liquid, which was isolated and purified by flash chromatography (silica gel, EtOAc/Hexane, 2/8) to afford the title compound, which was identified by IR, NMR and mass spectral analyses.

후처리

  1. customIn a three necked round bottom flask equipped with pressure
  2. customAfter the completion of reaction (TLC, 3-5 hours)
  3. customthe product was isolated by distillation under reduced pressure
  4. extractionThe residue was extracted with ethyl acetate (2×25 mL)
  5. washThe combined organic extracts were washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe organic layer was evaporated under vacuum
  8. customwhich was isolated
  9. custompurified by flash chromatography (silica gel, EtOAc/Hexane, 2/8)

출처 및 근거

ORD 기록
ord-9ca9b0b001ad42f6888f802779050f34
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875605B2

연결된 노트

불러오는 중…