Reacción #79913

Ecuación de reacción

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

Rendimiento 27.1%

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

Rendimiento 27.1%

Disolventes

ethanol

methanol

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

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
   Extracciónextracted with ethyl acetate (×2)
4. 4
   ExtracciónThe combined organic extract
5. 5
   Secadowas dried over anhydrous sodium sulfate
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated in vacuo
8. 8
   Otroto afford a solid
9. 9
   Otrothat was recrystallized from hot aqueous acetonitrile

Procedimiento

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 1 M 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%).

Fuente