反应 #1553

反应方程式

ether

water

5,6-diethyl-2-[3-(2-dioxolanyl)phenyl]-3-propargyl-4(3H)-pyrimidinone

hydrochloric acid

→

5,6-diethyl-2-(3-formylphenyl)-3-propargyl-4(3H)-pyrimidinone

收率 86.4%

溶剂

hexane

ethyl acetate

ethyl acetate

反应条件

后处理

1. 1
   workup.ADDITIONwere added to the reaction mixture
2. 2
   其他The layers were separated
3. 3
   萃取the aqueous layer was extracted twice with 50 mL of ether
4. 4
   干燥dried over MgSO4
5. 5
   浓缩concentrated

实验过程

To a solution of 2.3 g (6.8 mmol) of 5,6-diethyl-2-[3-(2-dioxolanyl)phenyl]-3-propargyl-4(3H)-pyrimidinone in 1 mL of ethyl acetate was added 50 mL of 6M hydrochloric acid and the mixture was stirred for 4 hours. The reaction was followed by gas chromatography and TLC(20% ethyl acetate in hexane). Upon completion of reaction, 75 mL of ether and 150 mL of water were added to the reaction mixture. The layers were separated and the aqueous layer was extracted twice with 50 mL of ether. The organic layers were combined, dried over MgSO4 and concentrated to yield 1.73 g of 5,6-diethyl-2-(3-formylphenyl)-3-propargyl-4(3H)-pyrimidinone (Compound 69) as a yellow oil (86%), which solidified on standing. Mp.=82°-86° C. 1H-NMR (CDCl3) δ 1.25(6H,m), 2.4(1H,t), 2.65(4H,q), 4.6(2H,d), 7.7(1H,t), 8.05(2H,m), 8.25(1H,s), 10.15(1H,s).

来源