Реакция #60216

Уравнение реакции

Diethyl (2Z)-3-phenylpent-2-ene-1,5-dioate

NaH

ethyl formate

→

diethyl (3E)-2-(hydroxymethylene)-3-phenylpent-3-ene-1,5-dioate

Выход 97.0%

Растворители

Et2O

Et2O

Et2O

Условия реакции

Обработка

1. 1
   Температураwere refluxed under argon for 15 min
2. 2
   ТемператураThe reaction was heated
3. 3
   Промывкаwashed with sat. NH4Cl (40 ml), half sat. NH4Cl (40 ml), brine (20 ml)
4. 4
   Сушкаdried with Na2SO4
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated under reduced pressure

Методика

A stirred mixture of NaH (158.4 mg, 6.6 mmol) and ethyl formate (1.07 ml, 13.2 mmol) in Et2O (5 ml) were refluxed under argon for 15 min. Diethyl (2Z)-3-phenylpent-2-ene-1,5-dioate in Et2O (5 ml) was added dropwise to the above solution over 5 min at rt. The reaction was heated to retlux for 12 hours. The heterogeneous yellow mixture was diluted with Et2O (100 ml), washed with sat. NH4Cl (40 ml), half sat. NH4Cl (40 ml), brine (20 ml), dried with Na2SO4, filtered, and concentrated under reduced pressure. The product diethyl (3E)-2-(hydroxymethylene)-3-phenylpent-3-ene-1,5-dioate was obtained in 97% yield and could be used without further purification.

Источник