Methanesulfonyl chloride → (R)-(tetrahydrofuran-2-yl)methyl methanesulfonate

HRID 1963964Notes

Reaction equation

HRID 1963964 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]>C(Cl)Cl>[CH3:8][S:9]([O:7][CH2:6][C@H:2]1[CH2:3][CH2:4][CH2:5][O:1]1)(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 6931745(2R)-oxolan-2-ylmethanol

Product 1

HCID 18649742(R)-(tetrahydrofuran-2-yl)methyl methanesulfonateYield 92.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (R)-(tetrahydrofuran-2-yl)methanol (600 mg, 5.87 mmol), DCM (35 ml), TEA (0.983 ml, 7.05 mmol) was diluted with methanesulfonyl chloride (0.467 ml, 5.99 mmol), via a dropwise addition. The reaction mixture was stirred at ambient temperature for 5 hours and the reaction progress was followed by LCMS. The crude reaction mixture was washed with saturated sodium bicarbonate (1×), water (2×), filtered and concentrated to a constant mass, giving 980 mg of the title compound, which was used without further purification. LCMS (m/z): 181.0 (MH+), retention time=0.40 min

Workup

  1. customThe crude reaction mixture
  2. washwas washed with saturated sodium bicarbonate (1×), water (2×)
  3. filtrationfiltered
  4. concentrationconcentrated to a constant mass

Sources & evidence

ORD record
ord-48e1598afde14f59b7095b01466c9a76
Source dataset
uspto-grants-2013_04
Patent number
US08415381B2

Reaction notes

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