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

HRID 2389898ノート

反応式

HRID 2389898 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 3283Diethyl Ether溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-3acea312adb044df8c716aa802acb4c0
出典データセット
uspto-grants-2012_09
特許番号
US08273761B2

反応ノート

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