Реакция #1553

Уравнение реакции

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

Выход 86.4%

Растворители

hexane

ethyl acetate

ethyl acetate

Условия реакции

Обработка

1. 1
   workup.ADDITIONwere added to the reaction mixture
2. 2
   ДругоеThe layers were separated
3. 3
   Экстракцияthe aqueous layer was extracted twice with 50 mL of ether
4. 4
   Сушкаdried over MgSO4
5. 5
   Концентрированиеconcentrated

Методика

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).

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