Reaktion #1715052

Reaktionsgleichung

[2-methyl-4-(m-tolyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]pentanoate

sodium hydroxide

methanol

→

title compound

Ausbeute 52.0%

2-[2-Methyl-4-(m-tolyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]pentanoic acid

Ausbeute 52.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Einengenthe reaction mixture was concentrated under reduced pressure
3. 3
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
4. 4
   WaschenThe organic layer was washed with brine, water
5. 5
   Trocknendried over magnesium sulphate
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigeThe crude residue was crystallized from a mixture ethyl acetate-heptane

Vorschrift

To a solution of methyl [[2-methyl-4-(m-tolyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]pentanoate (0.281 g; 0.65 mmol) in methanol (6.5 mL) was added a solution of sodium hydroxide 5 N (1.3 mL) and the mixture was heated at 60° C. for 18 h. After cooling, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and the mixture was acidified with HCl (1N) until pH 1. The organic layer was washed with brine, water, dried over magnesium sulphate and concentrated under reduced pressure. The crude residue was crystallized from a mixture ethyl acetate-heptane to furnish 0.129 g (52%) of the title compound as a light yellow solid.

Quelle