Sodium Thiosulfate → 3-Allyloxy-pyridine-2-carbaldehyde

HRID 1592380노트

반응식

HRID 1592380 반응식
[CH2:1]([O:4][C:5]1[C:6]([CH2:11][OH:12])=[N:7][CH:8]=[CH:9][CH:10]=1)[CH:2]=[CH2:3].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[CH2:1]([O:4][C:5]1[C:6]([CH:11]=[O:12])=[N:7][CH:8]=[CH:9][CH:10]=1)[CH:2]=[CH2:3]

참가 물질

6

반응물 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 14598977(3-Allyloxy-pyridin-2-yl)-methanol

생성물 1

HCID 450909933-Allyloxy-pyridine-2-carbaldehyde수율 98.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of (3-allyloxy-pyridin-2-yl)-methanol (2.08 g, 12.6 mmol) (Chen, Y. L. Eur. Pat. Appl. (1985), EP 150984) in CH2Cl2 (60 mL) was added Dess-Martin Periodinane (5.82 g, 13.7 mmol), and stirred at room temperature for 24 hours. CH2Cl2 (40 mL), saturated NaHCO3 (30 mL), and aqueous sodium thiosulfate (30 mL) were added and stirred for 40 minutes. The layers were separated and the aqueous phase was extracted with CH2Cl2 (2×50 mL). The combined organic extracts were washed with brine (1×75 mL), dried (Na2SO4), and concentrated to provide 2.02 g (98%) of 3-allyloxy-pyridine-2-carbaldehyde as a brown oil. 1H NMR (CDCl3) δ 4.71 (d, 2H, J=6.0 Hz), 5.37 (d, 1H, J=12.0 Hz), 5.50 (d, 1H, J=18.0 Hz), 5.99-6.12 (m, 1H), 7.38-7.48 (m, 2H), 8.40 (d, 1H, J=3.0 Hz), 10.41 (s, 1H).

후처리

  1. stirringstirred for 40 minutes
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with CH2Cl2 (2×50 mL)
  4. washThe combined organic extracts were washed with brine (1×75 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c1cfeef8b5b84c0bbdb6482a138618d2
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07291631B2

반응 노트

불러오는 중…