4-Toluenesulfonyl chloride → 2-Cyano-2-methylpropyl 4-methylbenzenesulfonate

HRID 237525Notes

Reaction equation

HRID 237525 reaction equation
[OH:1][CH2:2][C:3]([CH3:7])([CH3:6])[C:4]#[N:5].[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1>ClCCl.N1C=CC=CC=1.C(OCC)C>[CH3:18][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O:1][CH2:2][C:3]([C:4]#[N:5])([CH3:7])[CH3:6])(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

6

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 135313833-Hydroxy-2,2-dimethylpropanenitrile

Product 1

HCID 252194682-Cyano-2-methylpropyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-hydroxy-2,2-dimethylpropanenitrile (0.5 g) in dichloromethane (8 mL) and pyridine (1.5 mL) is added at 0° C. p-toluene-sulfonylchloride (1.0 g) in portions. The mixture is stirred for 12 hours at room temperature, diluted with diethylether and washed with 1 M aqueous HCl solution and brine. After drying (MgSO4) the solvent is evaporated and the residue is chromatographed on silica gel (petrole ether/ethyl acetate 90:10→50:50) to give the title compound. Yield: 770 mg; Mass spectrum (ESI+): m/z=254 [M+H]+.

Workup

  1. washwashed with 1 M aqueous HCl solution and brine
  2. dry with materialAfter drying (MgSO4) the solvent
  3. customis evaporated
  4. customthe residue is chromatographed on silica gel (petrole ether/ethyl acetate 90:10→50:50)

Sources & evidence

ORD record
ord-7760c5b69b944fd9ac03d81df9438a51
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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