4-Toluenesulfonyl chloride → HCID 86646873, compound
Reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH:4]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[CH2:5][CH2:6][OH:7].C(N(CC)CC)C.[CH3:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1>ClCCl>[CH3:1][O:2][C:3](=[O:16])[CH:4]([O:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=1)[CH2:5][CH2:6][O:7][S:31]([C:28]1[CH:29]=[CH:30][C:25]([CH3:24])=[CH:26][CH:27]=1)(=[O:33])=[O:32]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 22 °C
Procedure
To a solution of 2-(4-Chloro-phenoxy)-4-hydroxy-butyric acid methyl ester (Example 473b), 0.225 g) in dichloromethane (1.88 mL) at room temperature, was added triethylamine (116 mg) and 4-methylbenzene-1-sulfonyl chloride (177 mg). The mixture was stirred at 22° C. for 48 hr. The reaction mixture was partitioned between water and ethyl acetate. The phases were separated. The aqueous layer was extracted with ethyl acetate. The organic layers were washed with brine, dried over Na2SO4 and filtered. The crude mixture was concentrated to dryness and purified by chromatography on silica gel to yield the title compound as a colorless oil (169 mg; 46%). MS (ESI): m/z=419 [M+NH4]+.
Workup
- customThe reaction mixture was partitioned between water and ethyl acetate
- customThe phases were separated
- extractionThe aqueous layer was extracted with ethyl acetate
- washThe organic layers were washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationThe crude mixture was concentrated to dryness
- custompurified by chromatography on silica gel
Sources & evidence
- ORD record
- ord-97b0a693bcd24643b1ee9ce9536b9614
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08163793B2
Reaction notes
Loading…