Water → (R)-(tetrahydrofuran-2-yl)methyl methanesulfonate

HRID 1913809Notes

Reaction equation

HRID 1913809 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[CH2:6][OH:7].[CH3:8][S:9](Cl)(=[O:11])=[O:10].O>N1C=CC=CC=1>[O:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:6][O:7][S:9]([CH3:8])(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 637528(2S)-(+)-2-(Hydroxymethyl)tetrahydrofuran

Product 1

HCID 18649742(R)-(tetrahydrofuran-2-yl)methyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (S)-1-(tetrahydrofuran-2-yl)methanol (7.95 g) in pyridine (35 ml) was added, at −15° C., methanesulfonyl chloride (7.47 g), and the reaction was stirred at 0° C. for 5 hours. After the addition of water, the mixture was extracted with ethyl acetate. The organic phases were dried over magnesium sulfate and concentrated. The product was thus obtained with the molecular weight of 180.22 (C6H12O4S); MS (ESI): 181 (M+H+). Analogously, methanesulfonic acid (R)-1-(tetrahydrofuran-2-yl)methyl ester was synthesized.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic phases were dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe product was thus obtained with the molecular weight of 180.22 (C6H12O4S)

Sources & evidence

ORD record
ord-d2e5b055a6a04715bc1a49d79e9e2b31
Source dataset
uspto-grants-2013_12
Patent number
US08609731B2

Reaction notes

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