Sodium Thiosulfate → 3-(1H-Benzimidazol-1-yl)propanal

HRID 983612

반응식

HRID 983612 반응식
[N:1]1([CH2:10][CH2:11][CH2:12][OH:13])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[Na].C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl.C(OCC)(=O)C>[N:1]1([CH2:10][CH2:11][CH:12]=[O:13])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

참가 물질

7

반응물 4

HCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 128232803-(1H-Benzimidazol-1-yl)propan-1-ol

생성물 1

HCID 220185493-(1H-Benzimidazol-1-yl)propanal수율 81.6%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

3-(benzimidazol-1-yl)propan-1-ol (100 mg, 0.57 mmol) was dissolved in dichloromethane (6 mL), and treated with sodium periodinane (290 mg, 0.68 mmol). After stirring 5 hours, the mixture was treated with sodium bicarbonate (10 mL), ethyl acetate (10 mL), sodium thiosulfate (2 g) and extracted with ethyl acetate (2×10 mL). The organic phases were combined and washed with brine (15 mL), dried (MgSO4), filtered, and concentrated to yield the desired 3-(benzimidazol-1-yl)propanal (81 mg, 80%) as a yellow oil. 1H NMR (CDCl3) δ3.09 (t, 2H, J=6 Hz), 4.54 (t, 2H, J=6 Hz), 7.32 (m, 2H), 7.38 (m, 1H), 7.80 (d, 1H, J=6 Hz), 8.00 (s, 1H), 9.81 (s, 1H).

후처리

  1. extractionextracted with ethyl acetate (2×10 mL)
  2. washwashed with brine (15 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8974c0765f114cb18acf1ab88625dbd3
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06864265B2

연결된 노트

불러오는 중…