Pyridine → (S)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzenesulfonate

HRID 1358490Notes

Reaction equation

HRID 1358490 reaction equation
[CH3:1][C:2]1([CH3:10])[O:6][C@@H:5]([CH2:7][CH2:8][OH:9])[CH2:4][O:3]1.N1C=CC=CC=1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>ClCCl>[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23]([O:9][CH2:8][CH2:7][C@H:5]2[CH2:4][O:3][C:2]([CH3:10])([CH3:1])[O:6]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 110518052-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethan-1-ol

Product 1

HCID 12486298(S)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzenesulfonateYield 67,699.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol (50.89 g, 0.348 mol) and pyridine (113 ml, 1.39 mol) in dichloromethane (500 ml) was added gradually p-toluenesulfonyl chloride (79.65 g, 0.418 mmol) at ice-bath temperature. After removal of ice-bath, the reaction mixture was stirred at ambient temperature overnight. The mixture was poured into ice-cooled 1N-HCl (400 ml) and the mixture was extracted with dichloromethane. The organic layer was washed with saturated NaHCO3 solution and brine, dried with MgSO4, and concentrated in vacuo. The residue was purified by silica gel (800 g) column chromatography eluting with toluene/ethyl acetate (50:1 to 10:1) to give 2-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl p-toluenesulfonate (85.0 g, 81.3%) as an oil.

Workup

  1. customAfter removal of ice-bath
  2. additionThe mixture was poured into ice-
  3. temperaturecooled 1N-HCl (400 ml)
  4. extractionthe mixture was extracted with dichloromethane
  5. washThe organic layer was washed with saturated NaHCO3 solution and brine
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel (800 g) column chromatography
  9. washeluting with toluene/ethyl acetate (50:1 to 10:1)

Sources & evidence

ORD record
ord-c8b3871e91374389b9daf7dbd1ecc0e5
Source dataset
uspto-grants-2003_07
Patent number
US06596738B1

Reaction notes

Loading…