Triethylamine → Oxan-4-yl methanesulfonate

HRID 1838947Notes

Reaction equation

HRID 1838947 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[O:6]1[CH2:11][CH2:10][CH:9]([OH:12])[CH2:8][CH2:7]1.C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:12][CH:9]1[CH2:10][CH2:11][O:6][CH2:7][CH2:8]1)(=[O:4])=[O:3]

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 6344DichloromethaneSolvent

Procedure

Methanesulphonyl chloride (1.82 ml, 23.5 mmol) was added dropwise over 10 minutes to an ice-cold solution of tetrahydro-2H-pyran-4-ol (2.0 g, 19.6 mmol) and triethylamine (3.56 ml, 25.5 mmol) in dichloromethane (20 ml), and the reaction then stirred at room temperature for 72 hours. The reaction was washed with saturated aqueous sodium bicarbonate solution (10 ml), dried (MgSO4) and evaporated under reduced pressure to give an orange oil, that solidified on standing, 3.1 g.

Workup

  1. customthe reaction
  2. washThe reaction was washed with saturated aqueous sodium bicarbonate solution (10 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. customto give an orange oil

Sources & evidence

ORD record
ord-30288562da604d3d8c332cf090f937ef
Source dataset
uspto-grants-2004_01
Patent number
US06677335B1

Reaction notes

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