反応 #1551

反応方程式

phosphorous pentoxide

2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone

dimethoxymethane

phosphorous pentoxide

sodium hydroxide

→

3-methoxymethyl-2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone

収率 32.8%

溶媒

chloroform

methylene chloride

hexane

ethyl acetate

反応条件

後処理

1. 1
   その他at room temperature
2. 2
   workup.ADDITIONThe reaction mixture was poured
3. 3
   workup.ADDITIONwere added
4. 4
   その他The layers were separated
5. 5
   抽出the aqueous layer was extracted twice with methylene chloride
6. 6
   洗浄washed with brine
7. 7
   乾燥dried over MgSO4
8. 8
   濃縮concentrated
9. 9
   その他to yield 1.1 g crude product, which
10. 10
    その他was purified by recrystallization from hexane

実験手順

To a solution of 1.5 g (5.9 mmol) of 2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone, 17.2 g (226.3 mmol) dimethoxymethane, and 35 mL of chloroform was added 2.5 g (17.6 mmol) phosphorous pentoxide, at room temperature. By TLC (25% ethyl acetate in hexane) the reaction was incomplete after 4 h and an additional 3 g (21.1 mmol) phosphorous pentoxide was added. Stirring was continued for 16 h. The reaction mixture was poured onto crushed ice and 1M sodium hydroxide and methylene chloride were added. The layers were separated and the aqueous layer was extracted twice with methylene chloride. The organic extracts were combined and washed with brine, then dried over MgSO4 and concentrated to yield 1.1 g crude product, which was purified by recrystallization from hexane. Thus, 0.55 g (32%) 3-methoxymethyl-2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone (Compound 6) as a yellow solid was obtained. 1H-NMR (CDCl3) δ 3.55(3H,s); 5.2(2H,d); 6.85(1H,s); 7.65(3H,m); 7.75(2H,m).

出典