Réaction #43413

Équation de réaction

sodium sulphite

sodium hypochlorite

3,7-difluoro-8-(1-methylethenyl)-2-(methyloxy)-1,5-naphthyridine

cerium(III) chloride heptahydrate

→

8-[1-(Chloromethyl)ethenyl]-3,7-difluoro-2-(methyloxy)-1,5-naphthyridine

Solvants

tert-butanol

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGAfter 15 minutes stirring the mixture
2. 2
   Extractionwas extracted with ether (3×200 ml)
3. 3
   SéchageThe combined organic extracts were dried over magnesium sulphate
4. 4
   Autreevaporated
5. 5
   AutreThe residue was chromatographed on silica eluting a gradient of 0-50% ethyl acetate in hexane affording a white solid (320 mg, 34%)

Mode opératoire

A solution of 3,7-difluoro-8-(1-methylethenyl)-2-(methyloxy)-1,5-naphthyridine (820 mg, 3.5 mmol) in tert-butanol (50 ml) under argon was treated with cerium(III) chloride heptahydrate (1.29 g, 3.5 mmol) followed by a solution of sodium hypochlorite (12% w/v, 2.6 ml, 4.2 mmol). After 30 minutes stirring, saturated aqueous sodium sulphite solution (20 ml) was added. After 15 minutes stirring the mixture was extracted with ether (3×200 ml). The combined organic extracts were dried over magnesium sulphate and evaporated. The residue was chromatographed on silica eluting a gradient of 0-50% ethyl acetate in hexane affording a white solid (320 mg, 34%).

Source