Methanesulfonyl chloride → (S)-1-(tetrahydrofuran-2-yl)methyl methanesulfonate

HRID 69432Notes

Reaction equation

HRID 69432 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

HCID 31297Methanesulfonyl chlorideHCID 637528(2S)-(+)-2-(Hydroxymethyl)tetrahydrofuran

Product 1

HCID 18649743(S)-1-(tetrahydrofuran-2-yl)methyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with a solution of potassium hydrogensulfate (20%) and with a solution of saturated sodium hydrogencarbonate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c239c99e0dac47eabc6971ad83b5e709
Source dataset
uspto-grants-2014_09
Patent number
US08822495B2

Reaction notes

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