(2-Chloro-phenyl)-[3-(2-trimethylsilanyl-ethoxymethoxy)-pyridin-2-yl]-methanol → (2-Chloro-phenyl)-[3-(2-trimethylsilanyl-ethoxymethoxy)-pyridin-2-yl]-methanone

HRID 2251989Notes

Reaction equation

HRID 2251989 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:10]1[C:15]([O:16][CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])=[CH:14][CH:13]=[CH:12][N:11]=1)[OH:9]>C1(C)C=CC=CC=1.[O-2].[Mn+2]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[C:15]([O:16][CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])=[CH:14][CH:13]=[CH:12][N:11]=1)=[O:9]

Participants

4

Reactant 1

HCID 69154364(2-Chloro-phenyl)-[3-(2-trimethylsilanyl-ethoxymethoxy)-pyridin-2-yl]-methanol

Product 1

HCID 69153886(2-Chloro-phenyl)-[3-(2-trimethylsilanyl-ethoxymethoxy)-pyridin-2-yl]-methanoneYield 50.1%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 1140TolueneSolvent

Procedure

Add manganese oxide (II) (463 mg, 5.33 mmol) to a solution of (2-chloro-phenyl)-[3-(2-trimethylsilanyl-ethoxymethoxy)-pyridin-2-yl]-methanol (390 mg, 1.07 mmol) in toluene (20 mL), heat to reflux overnight. Filter mixture through Celite® and concentrate. Purify the residue by flash chromatography on silica gel eluting with 0-20% EtOAc/hexanes to afford the title compound (195 mg, 49%) as pink oil. MS(IS) 364 (M+1). TLC: Rf=0.45 (35% EtOAc/hexanes).

Workup

  1. temperatureheat
  2. temperatureto reflux overnight
  3. filtrationFilter mixture through Celite®
  4. concentrationconcentrate
  5. customPurify the residue by flash chromatography on silica gel eluting with 0-20% EtOAc/hexanes

Sources & evidence

ORD record
ord-491d0941f32842c794096bf9b59a3ada
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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