Chlorosulfonic acid → 4-(4-Methyl-tetrahydro-pyran-4-yl)-benzenesulfonyl Chloride

HRID 29524Notes

Reaction equation

HRID 29524 reaction equation
[CH3:1][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[Cl:14][S:15](O)(=[O:17])=[O:16]>C(Cl)Cl>[CH3:1][C:2]1([C:8]2[CH:13]=[CH:12][C:11]([S:15]([Cl:14])(=[O:17])=[O:16])=[CH:10][CH:9]=2)[CH2:3][CH2:4][O:5][CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 134955864-Methyl-4-phenyl-tetrahydro-pyran

Product 1

HCID 597886004-(4-Methyl-tetrahydro-pyran-4-yl)-benzenesulfonyl Chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a magnetically stirred mixture of 4-methyl-4-phenyl-tetrahydro-pyran (1.10 g, 6.24 mmol) in dry methylene chloride (50 mL) cooled in an ice bath was added 2.07 mL of chlorosulfonic acid (3.64 g, 31.2 mmol) dropwise under dry nitrogen. The reaction was stirred overnight at room temperature; the reaction was added to ice and the product was extracted with methylene chloride (3×100 mL). The organic layer was washed with saturated brine, dried (MgSO4), filtered and concentrated. e product was chromatographed on silica gel using ethyl acetate-hexane mixtures (2-20% hexane). Removal of solvent provided pure product as a colorless syrup which crystallized on standing: 1H NMR (CDCl3) δ 7.99 (d, 2H, J=8.8 Hz), 7.56 (d, 2H, J=8.8 Hz), 3.79 (ddd, 1H, J=11.7 Hz, J=8.4 Hz, J=3.3 Hz), 3.70 (ddd, 1H, J=11.7 Hz, J=6.0 Hz, J=3.8 Hz), 2.11 (ddd, 1H, J=13.8 Hz, J=8.4 Hz, J=3.8 Hz), 1.81 (dm, 1H, J=13.8 Hz), 1.35 (s, 3H). MS: m/z 275 (M++1).

Workup

  1. temperaturecooled in an ice bath
  2. additionthe reaction was added to ice
  3. extractionthe product was extracted with methylene chloride (3×100 mL)
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custome product was chromatographed on silica gel
  9. customRemoval of solvent
  10. customprovided pure product as a colorless syrup which
  11. customcrystallized

Sources & evidence

ORD record
ord-bcc521c55fa74cdebfcc5155f4fef128
Source dataset
uspto-grants-2008_09
Patent number
US07420055B2

Reaction notes

Loading…