تفاعل #52346

معادلة التفاعل

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

المردود 27.1%

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

المردود 27.1%

المذيبات

ethanol

methanol

tetrahydrofuran

ظروف التفاعل

المعالجة

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
   استخلاصextracted with ethyl acetate (×2)
4. 4
   استخلاصThe combined organic extract
5. 5
   تجفيفwas dried over anhydrous sodium sulfate
6. 6
   ترشيحfiltered
7. 7
   أخرىevaporated in vacuo
8. 8
   أخرىto afford a solid
9. 9
   أخرىthat was recrystallized from hot aqueous acetonitrile

الإجراء التجريبي

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%).

المصدر