Reaktion #897

Reaktionsgleichung

Ethanol

NaH

m-trifluoromethyl-phenol

NaH

4,6-dichloro-2-methylthiopyrimidine

→

4-ethoxy-2-methylthio-6-[3-(trifluoromethyl)phenoxy]pyrimidine

Lösungsmittel

THF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONVII-23)(5.0 g, 0.0256 mol) was added
2. 2
   workup.ADDITIONwere added
3. 3
   TemperaturThe resulting solution was refluxed for about 7 hours
4. 4
   SonstigeThe reaction solution was partitioned between ethyl acetate and aqueous saturated sodium hydrogen carbonate
5. 5
   Sonstigeto separate an organic phase
6. 6
   WaschenThe organic phase was washed with aqueous saturated sodium chloride
7. 7
   Trocknendried over anhydrous sodium sulfate
8. 8
   Einengenconcentrated
9. 9
   Sonstigepurified on a silica gel column

Vorschrift

Ethanol (1.18 g, 0.0256×1.0 mol) and NaH (1.02 g, (ca.60% in mineral oil), 0.0256×1.0 mol) were dissolved in THF and 4,6-dichloro-2-methylthiopyrimidine (Compound No. VII-23)(5.0 g, 0.0256 mol) was added thereto. The resulting solution was stirred for about 30 minutes at room temperature. To this reaction solution, m-trifluoromethyl-phenol (6.23 g, 0.0256×1.5 mol), NaH (1.54 g, (ca.60% in mineral oil), 0.0256×1.5 mol), and KI (2.12 g, 0.0256×0.5 mol) dissolved in DMF were added. The resulting solution was refluxed for about 7 hours. The reaction solution was partitioned between ethyl acetate and aqueous saturated sodium hydrogen carbonate to separate an organic phase. The organic phase was washed with aqueous saturated sodium chloride, dried over anhydrous sodium sulfate and concentrated, and thereafter purified on a silica gel column.

Quelle