反応 #1553

反応方程式

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

収率 86.4%

溶媒

hexane

ethyl acetate

ethyl acetate

反応条件

後処理

1. 1
   workup.ADDITIONwere added to the reaction mixture
2. 2
   その他The layers were separated
3. 3
   抽出the aqueous layer was extracted twice with 50 mL of ether
4. 4
   乾燥dried over MgSO4
5. 5
   濃縮concentrated

実験手順

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).

出典