Pyridine → 3-Butynyl p-toluenesulfonate

HRID 538796Notes

Reaction equation

HRID 538796 reaction equation
[CH2:1]([OH:5])[CH2:2][C:3]#[CH:4].N1C=CC=CC=1.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>C(Cl)Cl>[CH3:22][C:12]1[CH:17]=[CH:16][C:15]([S:18]([O:5][CH2:1][CH2:2][C:3]#[CH:4])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 135663-Butyn-1-OL

Product 1

HCID 2720203-Butynyl p-toluenesulfonateYield 16%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 3-butyn-1-ol (0.5 g, 8.3 mmol) in CH2Cl2 (20 mL) and pyridine (1.7 mL, 33.2 mmol) was added p-toluenesulfonyl chloride (1.7 g, 8.7 mmol). This mixture was stirred at ambient temperature for 16 h then diluted with CH2Cl2 (20 mL) and quenched with aqueous 1% HCl (5 mL). The layers were separated and the organic layer was washed with aqueous 1% HCl (5 mL) and brine (5 mL). The organic layer was dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified via column chromatography (4:1 hexanes:EtOAc) to provide the title compound (0.30 g, 1.3 mmol, 16% yield). MS (DCI/NH3) m/z 242 (M+NH4)+.

Workup

  1. customquenched with aqueous 1% HCl (5 mL)
  2. customThe layers were separated
  3. washthe organic layer was washed with aqueous 1% HCl (5 mL) and brine (5 mL)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. custompurified via column chromatography (4:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-f6b5fdb6eb1344db8f4d457ab6120422
Source dataset
uspto-grants-2014_10
Patent number
US08865753B2

Reaction notes

Loading…