4-Toluenesulfonyl chloride → (3-Methyloxetan-3-yl)methyl 4-methylbenzenesulfonate

HRID 478919Notes

Reaction equation

HRID 478919 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH:12][CH2:13][C:14]1([CH3:18])[CH2:17][O:16][CH2:15]1>ClCCl.N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:12][CH2:13][C:14]2([CH3:18])[CH2:17][O:16][CH2:15]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 1378373-Methyl-3-oxetanemethanol

Product 1

HCID 5461213(3-Methyloxetan-3-yl)methyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

4-Toluenesulfonyl chloride (20 g, 105 mmol) was dissolved in a mixture of dichloromethane (DCM) (50 ml) and pyridine (50 ml) and cooled in an ice bath. 3-(hydroxymethyl)-3-methyloxetane (100 mmol, 9.9 mL) was added dropwise. The temperature was increased to 20° C. overnight. The solution was diluted with DCM (100 mL) and extracted with water. The organic phase was dried over magnesium sulfate and filtered. The volatile solvents were removed by evaporation. The remaining material was concentrated several times with toluene to remove the residual pyridine and then with chloroform to remove the residual toluene. Yield: 22 g of a white crystalline solid (92%). TLC: Rf(petroleum ether/ethyl acetate, 1:1) 0.56.

Workup

  1. temperaturecooled in an ice bath
  2. extractionextracted with water
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. customThe volatile solvents were removed by evaporation
  6. concentrationThe remaining material was concentrated several times with toluene
  7. customto remove the residual pyridine
  8. customwith chloroform to remove the residual toluene

Sources & evidence

ORD record
ord-2182a25d29114733ac89040319b1d21f
Source dataset
uspto-grants-2003_11
Patent number
US06642334B2

Reaction notes

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