Water → 2-phenyl-3-methyl-8-(1-(S)-methanesulfonyloxy-2-[tert-butyldimethylsilyloxy]ethyl)quinoline
Reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].C(N(CC)CC)C.[C:13]1([C:19]2[C:28]([CH3:29])=[CH:27][C:26]3[C:21](=[C:22]([C@H:30]([OH:40])[CH2:31][O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[CH:23]=[CH:24][CH:25]=3)[N:20]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>C(OCC)C>[C:13]1([C:19]2[C:28]([CH3:29])=[CH:27][C:26]3[C:21](=[C:22]([C@H:30]([O:40][S:1]([CH3:4])(=[O:3])=[O:2])[CH2:31][O:32][Si:33]([C:36]([CH3:37])([CH3:39])[CH3:38])([CH3:34])[CH3:35])[CH:23]=[CH:24][CH:25]=3)[N:20]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
2 ml (26 mmol) of mesyl chloride and 4 ml (27 mmol) of triethylamine are added sequentially, at 0° C., to a solution of 7 g (17.8 mmol) of 2-phenyl-3-methyl-8-(1-(S)-hydroxy-2-[tert-butyldimethylsilyloxy]ethyl)quinoline in 200 ml of ethyl ether. The solution rapidly turns cloudy and a white precipitate is formed. After stirring for one hour at ambient temperature, 150 ml of distilled water are added to the reaction medium and the aqueous phase is extracted with 3×200 ml of ethyl ether. The organic phases are combined, dried over magnesium sulfate, filtered and concentrated under vacuum to provide 8.4 g of 2-phenyl-3-methyl-8-(1-(S)-methanesulfonyloxy-2-[tert-butyldimethylsilyloxy]ethyl)quinoline in the form of a colorless oil, used without purification in the following stage. (Yield: quantitative)
Workup
- customThe solution rapidly turns cloudy and a white precipitate is formed
- extractionthe aqueous phase is extracted with 3×200 ml of ethyl ether
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-d45077d2d7834674939742c0aade12ff
- Source dataset
- uspto-grants-2003_09
- Patent number
- US06617336B1
Reaction notes
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