Methanesulfonyl chloride → Oxan-4-yl methanesulfonate

HRID 237450Notes

Reaction equation

HRID 237450 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.[CH3:8][S:9](Cl)(=[O:11])=[O:10]>O1CCCC1.C(N(CC)CC)C>[CH3:8][S:9]([O:7][CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)(=[O:11])=[O:10]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 74956Tetrahydro-4H-pyran-4-ol

Product 1

HCID 11344352Oxan-4-yl methanesulfonate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of tetrahydro-2H-pyran-4-ol (20 g) in tetrahydrofuran (150 mL) and triethylamine (28.5 mL) is slowly added methanesulfonyl chloride (15.5 mL), while keeping the temperature below 30° C. The mixture is stirred for 12 hours at room temperature. The precipitate is filtered off and washed twice with tetrahydrofuran. The combined organic phases are concentrated and partitioned between ethyl acetate and water. The organic phase is dried (Na2SO4) and concentrated to give the title compound. Yield: 29.4 g; TLC: rf=0.36 (silicagel, petrole ether/ethyl acetate 1:1); Mass spectrum (ESI+): m/z=198 [M+NH4]+.

Workup

  1. customthe temperature below 30° C
  2. filtrationThe precipitate is filtered off
  3. washwashed twice with tetrahydrofuran
  4. concentrationThe combined organic phases are concentrated
  5. custompartitioned between ethyl acetate and water
  6. dry with materialThe organic phase is dried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a6b265c757954030bc95a5d9f355d5c9
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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