4-Toluenesulfonyl chloride → Oxetan-3-yl 4-methylbenzene-1-sulfonate

HRID 659883Notes

Reaction equation

HRID 659883 reaction equation
[O:1]1[CH2:4][CH:3]([OH:5])[CH2:2]1.[C:6]1([CH3:16])[CH:11]=[CH:10][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:8][CH:7]=1>N1C=CC=CC=1>[O:1]1[CH2:4][CH:3]([O:5][S:12]([C:9]2[CH:10]=[CH:11][C:6]([CH3:16])=[CH:7][CH:8]=2)(=[O:14])=[O:13])[CH2:2]1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 9942117Oxetan-3-ol

Product 1

HCID 13153907Oxetan-3-yl 4-methylbenzene-1-sulfonateYield 64%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of oxetan-3-ol (1.0 g, 13.0 mmol) in anhydrous pyridine (25 mL) at room temperature was added 4-toluene sulfonyl chloride (3.09 g, 16.2 mmol). After stirring the reaction mixture for 18 hours at room temperature, the reaction mixture was concentrated under reduced pressure. The resulting residue was purified by flash chromatography over silica gel eluting with a gradient of 0 to 30% ethyl acetate in heptane to afford 1.9 g (62% yield) of the desired product as a white solid.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe resulting residue was purified by flash chromatography over silica gel eluting with a gradient of 0 to 30% ethyl acetate in heptane

Sources & evidence

ORD record
ord-840dc4cf369c4b4ebf7f2b703f48bd51
Source dataset
uspto-grants-2011_12
Patent number
US08080580B2

Reaction notes

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