2-Iodoxybenzoic acid → 3-[4-(Trimethylsilyl)-2,3-dihydrofuro[2,3-b]pyridin-5-yl]propanal

HRID 2389898노트

반응식

HRID 2389898 반응식
[CH3:1][Si:2]([CH3:17])([CH3:16])[C:3]1[C:8]([CH2:9][CH2:10][CH2:11][OH:12])=[CH:7][N:6]=[C:5]2[O:13][CH2:14][CH2:15][C:4]=12.I(C1C=CC=CC=1C(O)=O)(=O)=O>CS(C)=O.C(OCC)C>[CH3:17][Si:2]([CH3:1])([CH3:16])[C:3]1[C:8]([CH2:9][CH2:10][CH:11]=[O:12])=[CH:7][N:6]=[C:5]2[O:13][CH2:14][CH2:15][C:4]=12

참가 물질

5

반응물 2

HCID 1087942-Iodoxybenzoic acidHCID 591794443-[4-(Trimethylsilyl)-2,3-dihydrofuro[2,3-b]pyridin-5-yl]propan-1-ol

생성물 1

HCID 591794483-[4-(Trimethylsilyl)-2,3-dihydrofuro[2,3-b]pyridin-5-yl]propanal수율 87.8%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 3283Diethyl Ether용매

실험 절차

A mixture of 3-[4-(trimethylsilyl)-2,3-dihydrofuro[2,3-b]pyridin-5-yl]propan-1-ol (6.54 g, 26.0 mmol) and orthoiodoxybenzoic acid (9.47 g, 33.8 mmol) in dimethyl sulfoxide (80 mL) was stirred at room temperature for 5 hr. The reaction solution was diluted with diethyl ether, and the mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→70/30) to give the title compound (5.69 g, yield 87%).

후처리

  1. washthe mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→70/30)

출처 및 근거

ORD 기록
ord-3acea312adb044df8c716aa802acb4c0
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273761B2

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