Reaktion #66733

Reaktionsgleichung

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

Lösungsmittel

acetonitrile

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared
2. 2
   Temperaturwas heated
3. 3
   Temperaturto reflux
4. 4
   SonstigeThe resulting reaction mixture
5. 5
   Temperaturwas refluxed for another 1.5 hours
6. 6
   workup.ADDITIONwas added
7. 7
   TemperaturThe mixture was then refluxed for 1 hour
8. 8
   Sonstigeevaporated to dryness
9. 9
   workup.ADDITIONBrine was added to the residue
10. 10
    Extraktionthe aqueous phase was extracted with ethyl acetate
11. 11
    Trocknenthe combined organic extracts were dried over anhydrous sodium sulphate
12. 12
    Filtrationfiltered
13. 13
    Einengenconcentrated in vacuo

Vorschrift

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).

Quelle