Water → (S)-tetrahydrofuran-3-yl methanesulfonate

HRID 2283695Notes

Reaction equation

HRID 2283695 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[O:13]1[CH2:17][CH2:16][C@H:15]([OH:18])[CH2:14]1.O>C1(C)C=CC=CC=1>[CH3:8][S:9]([O:18][C@H:15]1[CH2:16][CH2:17][O:13][CH2:14]1)(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2733227(S)-(+)-3-Hydroxytetrahydrofuran

Product 1

HCID 57561588(S)-tetrahydrofuran-3-yl methanesulfonate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Triethylamine (2.05 mL) and methanesulfonyl chloride (1.05 mL) were added to a solution of (S)-tetrahydrofuran-3-ol (1.0 g) in toluene (10 mL), and the reaction solution was stirred at room temperature for 2 hours. Water was added to the reaction solution, then the reaction solution was extracted with toluene and washed with a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum to obtain (S)-tetrahydrofuran-3-yl methanesulfonate as a colorless oily substance.

Workup

  1. extractionthe reaction solution was extracted with toluene
  2. washwashed with a saturated saline solution
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. customthe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-7675bbc602f44ee19731084ba5f2af6f
Source dataset
uspto-grants-2015_09
Patent number
US09145414B2

Reaction notes

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