Reaktion #952076

Reaktionsgleichung

sodium hydride

benzyl alcohol

product

2,4-dichloro-3-(3-ethoxy-2-methyl-4-methylsulfonylbenzoyl)pyridine

benzyl oxide

→

2,4-dibenzyloxy-3-(3-ethoxy-2-methyl-4-methylsulfonylbenzoyl)pyridine

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepartitioned between ether and water
2. 2
   SonstigeThe organic layers were dried
3. 3
   Sonstigeevaporated
4. 4
   Sonstigeto yield 0.5 g of a crude product
5. 5
   SonstigeThis was purified via chromatography on silica gel using 25% ethyl acetate in hexanes as the eluant

Vorschrift

To a solution of the product of step (b) (0.49 g, 1.26 mmol) in 5 ml THF at -20° C. under nitrogen was added a slurry of benzyl oxide (73.78 mmol) generated from benzyl alcohol and oil free sodium hydride in 2 ml THF. The reaction mixture was allowed to warm to room temperature and stirred for several hours, then partitioned between ether and water. The organic layers were dried and evaporated to yield 0.5 g of a crude product. This was purified via chromatography on silica gel using 25% ethyl acetate in hexanes as the eluant to give 0.177 g of 2,4-dibenzyloxy-3-(3-ethoxy-2-methyl-4-methylsulfonylbenzoyl)pyridine, a viscous yellow oil.

Quelle