Reaktion #52346

Reaktionsgleichung

2-fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)benzoic acid ethyl ester

Compound 9

2-fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)benzoic acid ethyl ester

sodium hydroxide

→

title compound

Ausbeute 27.1%

2-Fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2yl-ethynyl)-benzoic acid

Ausbeute 27.1%

Lösungsmittel

ethanol

methanol

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISTILLATIONThe volatiles were distilled off in vacuo
2. 2
   workup.ADDITIONthe residue was diluted with water and dilute hydrochloric acid
3. 3
   Extraktionextracted with ethyl acetate (×2)
4. 4
   ExtraktionThe combined organic extract
5. 5
   Trocknenwas dried over anhydrous sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated in vacuo
8. 8
   Sonstigeto afford a solid
9. 9
   Sonstigethat was recrystallized from hot aqueous acetonitrile

Vorschrift

A solution of 2-fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)benzoic acid ethyl ester (Compound 9, 0.1 g, 0.274 mmol) in ethanol(4 mL), methanol (2 mL) and tetrahydrofuran (2 mL) was treated with 1M aqueous sodium hydroxide solution and heated at 70° C. for 1 h. The volatiles were distilled off in vacuo and the residue was diluted with water and dilute hydrochloric acid and extracted with ethyl acetate (×2). The combined organic extract was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford a solid that was recrystallized from hot aqueous acetonitrile to afford the title compound (0.025 g, 27%).

Quelle