Dimethyl Sulfate → HCID 19917146, compound

Reaction equation

[CH2:1]([N:3]([CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]2[CH:35]=[CH:34][S:33][CH:32]=2)[CH:26]=1)[CH2:4]/[CH:5]=[CH:6]/[C:7]#[C:8][C:9]([C:15]([F:18])([F:17])[F:16])([OH:14])[C:10]([F:13])([F:12])[F:11])[CH3:2].[H-].[Na+].S(OC)(O[CH3:42])(=O)=O>CN(C)C=O>[CH2:1]([N:3]([CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]2[CH:35]=[CH:34][S:33][CH:32]=2)[CH:26]=1)[CH2:4]/[CH:5]=[CH:6]/[C:7]#[C:8][C:9]([C:15]([F:18])([F:17])[F:16])([O:14][CH3:42])[C:10]([F:11])([F:12])[F:13])[CH3:2]

Participants

Procedure

159 mg of (E)-ethyl-N-(7,7,7-trifluoro-6-trifluoromethyl-6-hydroxy-2-hepten-4-ynyl)-2-[2-[3-(3-thienyl)phenoxy]ethoxy]ethylamine was dissolved in 2 ml of dimethylformamide, and 24 mg of 60% oily sodium hydride was added. The mixture was stirred at room temperature for 10 minutes. To this solution was added 60 μl of dimethyl sulfate, and then the mixture was stirred at room temperature for 4 hours. The solvent was evaporated under reduced pressure, and ethyl acetate and water were added to the residue to extract it. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The desiccant was separated by filtration, and the solvent was evaporated. The residue was purified by silica gel column chromatography [methylene chloride/methanol=70/1] to give 24 mg (yield 15%) of the captioned compound as a pale yellow oil.