Реакция #66733

Уравнение реакции

acetic acid

ethyl 3-bromo-2-(bromomethyl)propionate

triethylamine

3,6-dihydro-4-(1-pyrrolidinyl)-2H-thiopyran

→

9-oxo-3-thia-bicyclo[3.3.1]nonane-7-carboxylic acid ethyl ester

Растворители

acetonitrile

acetonitrile

Условия реакции

Обработка

1. 1
   Другоеprepared
2. 2
   Температураwas heated
3. 3
   Температураto reflux
4. 4
   ДругоеThe resulting reaction mixture
5. 5
   Температураwas refluxed for another 1.5 hours
6. 6
   workup.ADDITIONwas added
7. 7
   ТемператураThe mixture was then refluxed for 1 hour
8. 8
   Другоеevaporated to dryness
9. 9
   workup.ADDITIONBrine was added to the residue
10. 10
    Экстракцияthe aqueous phase was extracted with ethyl acetate
11. 11
    Сушкаthe combined organic extracts were dried over anhydrous sodium sulphate
12. 12
    Фильтрацияfiltered
13. 13
    Концентрированиеconcentrated in vacuo

Методика

A mixture of triethylamine (10.1 ml, 72 mmol) and 3,6-dihydro-4-(1-pyrrolidinyl)-2H-thiopyran (12.9 g, 76 mmol, prepared according to a procedure described in Tetrahedron Asymmetry 1997, 1811-1820) in anhydrous acetonitrile (55 ml) was heated to reflux, then ethyl 3-bromo-2-(bromomethyl)propionate (14.6 g, 53 mmol) in dry acetonitrile (42 ml) was added dropwise over a period of 45 min. The resulting reaction mixture was refluxed for another 1.5 hours, then cooled to room temperature before a 10% aqueous acetic acid solution (5.2 ml) was added. The mixture was then refluxed for 1 hour and evaporated to dryness. Brine was added to the residue, the aqueous phase was extracted with ethyl acetate, the combined organic extracts were dried over anhydrous sodium sulphate, filtered and concentrated in vacuo to yield 9-oxo-3-thia-bicyclo[3.3.1]nonane-7-carboxylic acid ethyl ester as a brown oil (15.5 g).

Источник