Potassium Hydroxide → Rac-(3,4-dichloro-phenyl)-[(tetrahydro-pyran-4-yl)oxy]-acetic acid
Reaction equation
C[O:2][C:3](=[O:20])[CH:4]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)[O:5][CH:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1.[OH-].[K+]>C(O)C.O>[Cl:19][C:14]1[CH:13]=[C:12]([CH:4]([O:5][CH:6]2[CH2:11][CH2:10][O:9][CH2:8][CH2:7]2)[C:3]([OH:20])=[O:2])[CH:17]=[CH:16][C:15]=1[Cl:18]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
A solution of rac-(3,4-dichloro-phenyl)-[(tetrahydro-pyran-4-yl)oxy]-acetic acid methyl ester (598 mg, 1.87 mmol) in ethanol (15 mL) was treated with a solution of potassium hydroxide (262 mg, 4.68 mmol) and water (2 mL) and the mixture was allowed to stir at 25° C. After 3 h, the reaction was diluted with water (10 mL) and the ethanol was removed in vacuo. The aqueous layer was then acidified to pH 2 with 1N hydrochloric acid and extracted with dichloromethane (3×15 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated under reduced pressure. The reaction product was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 95/5 chloroform/methanol plus 1% acetic acid) to afford rac-(3,4-dichloro-phenyl)-[(tetrahydro-pyran-4-yl)oxy]-acetic acid (544 mg, 95% yield) as a clear colorless oil: EI-HRMS m/e calcd for C13H14Cl2O4 (M+) 304.0269, found 304.0259.
Workup
- customthe ethanol was removed in vacuo
- extractionextracted with dichloromethane (3×15 mL)
- dry with materialThe combined organic layers were dried over sodium sulfate
- filtrationfiltered
- customevaporated under reduced pressure
- customThe reaction product was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 95/5 chloroform/methanol plus 1% acetic acid)
Sources & evidence
- ORD record
- ord-15c4a1d2bfb1433285641212ddfd276b
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06608218B2
Reaction notes
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