Triethylamine → Oxan-4-yl methanesulfonate

HRID 1798548Notes

Reaction equation

HRID 1798548 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.CCN(CC)CC.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(Cl)Cl>[O:1]1[CH2:6][CH2:5][CH:4]([O:7][S:16]([CH3:15])(=[O:18])=[O:17])[CH2:3][CH2:2]1

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

Tetrahydro-pyran-4-ol (1 eq, 4.9 mmol, 0.5 g) is dissolved in dry DCM (10 ml) under an inert atmosphere of argon. NEt3 (3 eq, 14.69 mmol, 2.047 ml) is then added at 0° C., followed by methanesulfonyl chloride (1.1 eq, 5.39 mmol, 0.417 ml) and the reaction mixture is stirred at room temperature overnight. The reaction mixture is quenched with NaHCO3 (1M, 3 ml) and extracted with DCM. This organic portion is washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo to afford the title compound.

Workup

  1. customThe reaction mixture is quenched with NaHCO3 (1M, 3 ml)
  2. extractionextracted with DCM
  3. washThis organic portion is washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-28f783d27be04f0b9f33dc380c443de4
Source dataset
uspto-grants-2013_01
Patent number
US08343966B2

Reaction notes

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