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

HRID 2389898Notes

Reaction equation

HRID 2389898 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-3acea312adb044df8c716aa802acb4c0
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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