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

HRID 2194585Notes

Reaction equation

HRID 2194585 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>C(Cl)Cl>[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([O:7][CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

4

Reactant 2

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

Product 1

HCID 13961807Tetrahydro-2H-pyran-4-yl 4-methylbenzenesulfonateYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tetrahydro-2H-pyran-4-ol (1 g, 9.8 mmole) and TEA (2 g, 19.6 mmole) in DCM (20 mL) was added 4-methylbenzene-1-sulfonyl chloride (1.8 g, 9.8 mmole) at 0° C. The mixture was stirred at room temperature for 8 h, washed with water, dried over MgSO4, filtered, and concentrated. The residue was purified by ISCO (silica gel, 15% ethyl acetate in hexane) to give the title compound (2.2 g, 89% yield) as white solid. MS (ESI) m/z: Found: 257.3 (M++1). Calc. 256.3 (M).

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by ISCO (silica gel, 15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-46e7a3b462ce4dbea1a761e9ccb33b93
Source dataset
uspto-grants-2012_12
Patent number
US08334292B1

Reaction notes

Loading…