4-Toluenesulfonyl chloride → Tetrahydro-2H-pyran-4-yl 4-methylbenzenesulfonate

HRID 1809381Notes

Reaction equation

HRID 1809381 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1>N1C=CC=CC=1.C(Cl)Cl>[O:1]1[CH2:6][CH2:5][CH:4]([O:7][S:14]([C:11]2[CH:12]=[CH:13][C:8]([CH3:18])=[CH:9][CH:10]=2)(=[O:16])=[O:15])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 74956Tetrahydro-4H-pyran-4-ol

Product 1

HCID 13961807Tetrahydro-2H-pyran-4-yl 4-methylbenzenesulfonateYield 90%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 133 g (1.31 mol) of tetrahydropyran-4-ol in pyridine (1.5 L) are added 373 g (1.95 mol) of p-toluenesulfonylchloride portionwise at 10° C. After complete addition the reaction is allowed to warm to room temperature and stirred for 18 h. The reaction is poured onto a stirred mixture of aqueous HCl/ice. The resulting precipitate is isolated by filtration and dissolved in DCM (1 L). The organic layer is washed with 1M aqueous HCl solution (1 L), followed by saturated aqueous NaHCO3 solution (1 L) and is then dried over Na2SO4. Filtration and concentration of the filtrate under reduced pressure gives 300 g of toluene-4-sulfonic acid tetrahydropyran-4-yl ester as an orange oil. Yield: 90%, ES-MS: m/z: 257 [M+H], 279 [M+Na]

Workup

  1. additionAfter complete addition the reaction
  2. customThe resulting precipitate is isolated by filtration
  3. washThe organic layer is washed with 1M aqueous HCl solution (1 L)
  4. dry with materialis then dried over Na2SO4
  5. filtrationFiltration and concentration of the filtrate under reduced pressure

Sources & evidence

ORD record
ord-2a079b46d27f4e6dae978f45e307c470
Source dataset
uspto-grants-2013_01
Patent number
US08362039B2

Reaction notes

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