4-Toluenesulfonyl chloride → 2-(tetrahydro-2H-pyran-4-yl)ethyl 4-methylbenzenesulfonate

HRID 1802375Notes

Reaction equation

HRID 1802375 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][OH:9])[CH2:3][CH2:2]1.[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>N1C=CC=CC=1>[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][O:9][S:16]([C:13]2[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=2)(=[O:18])=[O:17])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 177509442-(Oxan-4-yl)ethan-1-ol

Product 1

HCID 592679642-(tetrahydro-2H-pyran-4-yl)ethyl 4-methylbenzenesulfonateYield 53.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1.63 g (12.5 mmol) of 2-(tetrahydro-pyran-4-yl)-ethanol in pyridine (15 mL) are added 3.58 g (18.8 mmol) of p-toluenesulfonylchloride. The reaction is stirred at room temperature for 5 h. The reaction mixture is concentrated under reduced pressure. The residue is dissolved 2M aqueous HCl solution (20 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts are dried over Na2SO4, filtered and the solvent is removed to give 1.9 g of toluene-4-sulfonic acid 2-(tetrahydro-pyran-4-yl)-ethyl ester as off-white crystalline solid. Yield: 53%; ES-MS: m/z 285 [M+H]

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. dissolutionThe residue is dissolved 2M aqueous HCl solution (20 mL)
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. dry with materialThe combined organic extracts are dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent is removed

Sources & evidence

ORD record
ord-174b9f7698d344bf87e6968aea5097ab
Source dataset
uspto-grants-2013_01
Patent number
US08349871B2

Reaction notes

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