Water → HCID 15635484, compound

HRID 2116509Notes

Reaction equation

HRID 2116509 reaction equation
I(C1C=CC=CC=1C(O)=O)(=O)=O.C(C1C=CC(C([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][C:24]=2[O:29][CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])O)=CC=1)C.O>CS(C)=O.O1CCCC1>[CH3:35][Si:34]([CH3:37])([CH3:36])[CH2:33][CH2:32][O:31][CH2:30][O:29][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:23]=1

Participants

6

Reactant 3

HCID 962WaterHCID 1087942-Iodoxybenzoic acidHCID 69220218HCID 69220218, compound

Product 1

HCID 15635484HCID 15635484, compoundYield 180.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of o-iodoxybenzoic acid (IBX) in dimethyl sulfoxide (15 mL), a solution of (4-ethylphenyl)-[3-[2-(trimethylsilyl)ethoxymethoxy]pyridin-4-yl]-methanol (synthesized in Reference Example 6; 3.0 g, 8.34 mmol) in tetrahydrofuran (20 mL) was added and the reaction mixture was stirred at room temperature for 17.5 hours. Water was added to the reaction mixture and the resulting precipitate was filtered and washed with ethyl acetate. The filtrate was washed with water and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give 4-(4-ethylbenzoyl)-[3-[2-(trimethylsilyl)ethoxymethoxy]pyridine (3.4 g).

Workup

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with ethyl acetate
  3. washThe filtrate was washed with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5a47e1388ac34e69a32a7de7bfd55a4a
Source dataset
uspto-grants-2008_10
Patent number
US07439232B2

Reaction notes

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