Potassium Hydroxide → HCID 53348310, compound
Reaction equation
C([O:3][C:4](=[O:23])[C:5]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[C:14]([Cl:22])[CH:13]=1)=[CH:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)C.[OH-].[K+]>C(O)C.O>[Cl:22][C:14]1[CH:13]=[C:12](/[C:5](=[CH:6]\[CH:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)/[C:4]([OH:23])=[O:3])[CH:17]=[CH:16][C:15]=1[S:18]([CH3:21])(=[O:20])=[O:19]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
A solution of the isomeric mixture of 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-acrylic acid ethyl ester [500 mg, 1.40 mmol, (E):(Z)=2:1] in ethanol (16 mL) was treated with a solution of potassium hydroxide (393.6 mg, 7.00 mmol) in water (3.7 mL). The yellow solution was stirred for 3 h at 25° C. and then concentrated in vacuo to remove the ethanol. The remaining aqueous layer was acidified to pH=2 with a 1N aqueous hydrochloric acid solution and then extracted with methylene chloride (3×15 mL). The combined organic layers were then dried over sodium sulfate, filtered and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 75/25 hexanes/ethyl acetate plus 1% acetic acid) afforded (E)-2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-acrylic acid (458 mg, 99%, 95% is the E isomer) as a white foam: FAB-HRMS m/e calcd for C15H17ClO4S (M+H)+329.0614, found 329.0628.
Workup
- concentrationconcentrated in vacuo
- customto remove the ethanol
- extractionextracted with methylene chloride (3×15 mL)
- dry with materialThe combined organic layers were then dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-31c5c49fe3c44ec8ae16bb0cd2153988
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06353111B1
Reaction notes
Loading…