4-Toluenesulfonyl chloride → Oxetan-3-yl 4-methylbenzene-1-sulfonate

HRID 1848220Notes

Reaction equation

HRID 1848220 reaction equation
[O:1]1[CH2:4][CH:3]([OH:5])[CH2:2]1.[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1>C(Cl)Cl>[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([O:5][CH:3]2[CH2:4][O:1][CH2:2]2)(=[O:15])=[O:14])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 9942117Oxetan-3-ol

Product 1

HCID 13153907Oxetan-3-yl 4-methylbenzene-1-sulfonateYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of oxetan-3-ol (0.85 g, 11.5 mmol) in DCM (38 mL) were added TEA (3.3 mL, 23 mmol) and 4-methylbenzene-1-sulfonyl chloride (2.7 g, 13.8 mmol). The reaction mixture was stirred at rt for 15 h. The mixture was partitioned between water and DCM. The organic layer was separated, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with a gradient of 30% DCM in petroleum ether to 100% DCM to afford oxetan-3-yl 4-methylbenzenesulfonate (1.3 g, 50%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.77 (d, J=8.4 Hz, 2H), 7.35 (d, J=8.7 Hz, 2H), 5.30 (m, 1H), 4.66-4.74 (m, 4H), 2.46 (s, 3H); LCMS (ESI) m/z 229 (M+H)+.

Workup

  1. customThe mixture was partitioned between water and DCM
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel flash chromatography
  7. washeluting with a gradient of 30% DCM in petroleum ether to 100% DCM

Sources & evidence

ORD record
ord-c61da02e09bb4195901f80f6112fc065
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

Loading…