4-Toluenesulfonyl chloride → (Oxan-3-yl)methyl 4-methylbenzene-1-sulfonate

HRID 78487

Reaction equation

HRID 78487 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][OH:8])[CH2:2]1.[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>C(Cl)Cl.N1C=CC=CC=1>[CH3:19][C:9]1[CH:14]=[CH:13][C:12]([S:15]([O:8][CH2:7][CH:3]2[CH2:4][CH2:5][CH2:6][O:1][CH2:2]2)(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 85769Tetrahydro-2H-pyran-3-methanol

Product 1

HCID 86618913(Oxan-3-yl)methyl 4-methylbenzene-1-sulfonate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (tetrahydropyran-3-yl)-methanol (Matrix, 1.67 g, 14.4 mmol) in 15 mL of CH2Cl2 and 15 mL of pyridine was added p-toluenesulfonyl chloride (2.9 g, 15.1 mmol) in portions over 10 minutes. The mixture stirred at ambient temperature for 18 hours and was quenched with 10 mL of saturated, aqueous NaHCO3. The layers were separated and the aqueous phase was extracted three 5 mL of portions of CH2Cl2. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification via column chromatography (SiO2, 70% hexanes in ethyl acetate) afforded the title compound. MS (DCI/NH3) m/z 288 (M+NH4)+.

Workup

  1. customwas quenched with 10 mL of saturated, aqueous NaHCO3
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted three 5 mL of portions of CH2Cl2
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification via column chromatography (SiO2, 70% hexanes in ethyl acetate)

Sources & evidence

ORD record
ord-25715a1446204b478a238d2771de1968
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Linked notes

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