Water → (1S)-1-propylheptyl p-toluenesulfonate
Reaction equation
[CH2:1]([C@@H:7]1[CH2:9][O:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:10]([Mg]Cl)[CH3:11].[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.O>O1CCCC1.[Cu](Cl)Cl.C(OCC)(=O)C.N1C=CC=CC=1>[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20]([O:8][C@@H:7]([CH2:9][CH2:10][CH3:11])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])(=[O:22])=[O:21])=[CH:16][CH:15]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- -20 °C
Procedure
(2R)-2-Hexyloxirane (1.22 mL, 100% ee) was added dropwise to a tetrahydrofuran (2.21 mL) solution of copper chloride (15.8 mg) at −20° C. under argon atmosphere, and then a 2.11 mol/L ethyl magnesium chloride in tetrahydrofuran solution (4.55 mL) was added dropwise thereto. The reaction mixture was stirred at −20° C. for 1.5 hours, and a tetrahydrofuran solution of p-toluenesulfonyl chloride (1.83 g) was added dropwise thereto, followed by stirring for 1.5 hours. Then, the temperature was raised up to 0° C., followed by stirring for 3.5 hours. To the reaction solution were added water and pyridine, followed by stirring at 0° C. for 40 minutes, ethyl acetate was added thereto and the mixture was successively washed with 10% sulfuric acid (twice), water and brine and concentrated to give the title compound (2.27 g) having the following physical data.
Workup
- stirringby stirring for 1.5 hours
- temperatureThen, the temperature was raised up to 0° C.
- stirringby stirring for 3.5 hours
- stirringby stirring at 0° C. for 40 minutes
- washthe mixture was successively washed with 10% sulfuric acid (twice), water and brine
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-45710ffc796440f0b95ffc1d85a00d0d
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07589221B2
Reaction notes
Loading…