Sodium Hydroxide → 2-Fluoro-4-(8,8-dimethl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2yl-ethynyl)-benzoic Acid
Reaction equation
C([O:3][C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:22]=[CH:21][C:20]3[C:19](=[O:23])[CH2:18][CH2:17][C:16]([CH3:25])([CH3:24])[C:15]=3[CH:14]=2)=[CH:7][C:6]=1[F:26])C.[OH-].[Na+]>C(O)C.CO.O1CCCC1>[F:26][C:6]1[CH:7]=[C:8]([C:11]#[C:12][C:13]2[CH:22]=[CH:21][C:20]3[C:19](=[O:23])[CH2:18][CH2:17][C:16]([CH3:25])([CH3:24])[C:15]=3[CH:14]=2)[CH:9]=[CH:10][C:5]=1[C:4]([OH:27])=[O:3]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 70 °C
Procedure
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%).
Workup
- distillationThe volatiles were distilled off in vacuo
- additionthe residue was diluted with water and dilute hydrochloric acid
- extractionextracted with ethyl acetate (×2)
- extractionThe combined organic extract
- dry with materialwas dried over anhydrous sodium sulfate
- filtrationfiltered
- customevaporated in vacuo
- customto afford a solid
- customthat was recrystallized from hot aqueous acetonitrile
Sources & evidence
- ORD record
- ord-a89051562e64455ba36678f97f74894e
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06603019B2
Reaction notes
Loading…