Reacción #2028886

Ecuación de reacción

4-(2-Thienyl)butyric acid

acetic anhydride

phosphoric acid

→

oil

Rendimiento 88.9%

4-keto-4,5,6,7-tetrahydrothianaphthene

Rendimiento 88.9%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturato reflux for 3.2 hours
3. 3
   Extracciónextracted with ethyl acetate
4. 4
   Lavadowashed with brine
5. 5
   Secadodried over MgSO4
6. 6
   Concentraciónconcentrated in vacuo

Procedimiento

4-(2-Thienyl)butyric acid (28.42 g, 167 mmol) was placed in a round bottom flask with acetic anhydride (30 mL) and phosphoric acid (0.6 mL), and heated to reflux for 3.2 hours. The reaction mixture was poured into 100 mL of water, extracted with ethyl acetate, washed with brine, dried over MgSO4, and concentrated in vacuo to give a brown oil (22.60 g) which was vacuum distilled (1 mm Hg, 107°-115° C.) to give a white solid (13.08 g, 51%): mp 34°-40° C.); 1H NMR (CDCl3) 300 MHz 7.29 (d, J=5.2 Hz, 1H), 6.99 (d, J=5.2 Hz, 1H, 2.95 (t, J=6.0 Hz, 2H), 2.47(m, 2H), 2.13(m, 2H). M+H=153.

Fuente