Reacción #52346

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 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%).

Fuente