Methanesulfonyl chloride → (S)-1-(tetrahydrofuran-2-yl)methyl methanesulfonate
Reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[O:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[CH2:11][OH:12]>N1C=CC=CC=1>[O:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[CH2:11][O:12][S:1]([CH3:4])(=[O:3])=[O:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Mesylchloride (12.1 g) was added to a mixture of (S)-1-(Tetrahydro-furan-2-yl)-methanol (10.0 g) and pyridine (55 mL) at −15° C. and stirred for 1.5 hours at room temperature. The mixture was poured into ice water and extracted with ethyl acetate. The organic phase was washed with a solution of potassium hydrogensulfate (20%) and with a solution of saturated sodium hydrogencarbonate, dried over magnesium sulfate and concentrated.
Workup
- extractionextracted with ethyl acetate
- washThe organic phase was washed with a solution of potassium hydrogensulfate (20%) and with a solution of saturated sodium hydrogencarbonate
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c239c99e0dac47eabc6971ad83b5e709
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822495B2
Reaction notes
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