Reaktion #1715041

Reaktionsgleichung

HCl

methyl [2-methyl-4-(2-thienyl)-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-b]pyridin-3-yl]pentanoate

sodium hydroxide

→

title compound

Ausbeute 72.5%

2-[2-Methyl-4-(2-thienyl)-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-b]pyridin-3-yl]pentanoic acid

Ausbeute 72.5%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Einengenpartially concentrated under reduced pressure
3. 3
   SonstigeThe residue was partitioned between ethyl acetate and water
4. 4
   WaschenThe organic layer was washed with brine
5. 5
   Trocknendried over sodium sulphate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   SonstigeThe residue was crystallized from a mixture of ethyl acetate/heptane

Vorschrift

To a solution of methyl [2-methyl-4-(2-thienyl)-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-b]pyridin-3-yl]pentanoate (0.249 g, 0.646 mmol) in methanol (6.5 mL) was added a solution of sodium hydroxide 10 N (0.65 ml) and the mixture was heated at 100° C. for 18 h in a sealed tube. After cooling, the reaction mixture was acidified with 1N HCl (pH˜2) and partially concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was crystallized from a mixture of ethyl acetate/heptane to afford 0.174 g (72%) of the title compound as a white solid.

Quelle