Pyridine → (1-Cyanocyclopropyl)methyl 4-methylbenzenesulfonate

HRID 1497362Notes

Reaction equation

HRID 1497362 reaction equation
[OH:1][CH2:2][C:3]1([C:6]#[N:7])[CH2:5][CH2:4]1.N1C=CC=CC=1.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>ClCCl>[CH3:24][C:14]1[CH:19]=[CH:18][C:17]([S:20]([O:1][CH2:2][C:3]2([C:6]#[N:7])[CH2:5][CH2:4]2)(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 220282071-(Hydroxymethyl)cyclopropane-1-carbonitrile

Product 1

HCID 22028201(1-Cyanocyclopropyl)methyl 4-methylbenzenesulfonateYield 38.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(hydroxymethyl)cyclopropanecarbonitrile (1.0 g) in dichloromethane (15 ml) was added pyridine (4.1 ml) at 0° C., and the mixture was stirred at the same temperature for 15 min. To the obtained reaction mixture was added dropwise p-toluenesulfonyl chloride (3.9 g), and the mixture was stirred at room temperature for 16 hr. The reaction mixture was concentrated under reduced pressure, water was added, and the mixture was extracted with dichloromethane. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (1 g).

Workup

  1. customTo the obtained reaction mixture
  2. stirringthe mixture was stirred at room temperature for 16 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure, water
  4. additionwas added
  5. extractionthe mixture was extracted with dichloromethane
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3f0fe0a308c04c2e9f2c24dd635777f7
Source dataset
uspto-grants-2015_12
Patent number
US09199963B2

Reaction notes

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