Triethylamine → Oxan-4-yl methanesulfonate

HRID 1620723Notes

Reaction equation

HRID 1620723 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>ClCCl>[CH3:15][S:16]([O:7][CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 74956Tetrahydro-4H-pyran-4-ol

Product 1

HCID 11344352Oxan-4-yl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tetrahydro-2H-pyran-4-ol (10.0 g) and triethylamine (19.1 mL) in dichloromethane (100 mL) was added dropwise methanesulfonyl chloride (10.7 mL) under ice-cooling. The reaction mixture was stirred at room temperature for 1 hr, and dichloromethane was added. The organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (16.2 g).

Workup

  1. temperaturecooling
  2. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c307699256854e88ab6b14ac9ec27111
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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