Water → HCID 323833, compound

HRID 660756Notes

Reaction equation

HRID 660756 reaction equation
C1(C)C=CC(S(O[CH2:11][C:12]([CH3:26])([CH3:25])[CH2:13][O:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])(=O)=O)=CC=1.[C-:28]#[N:29].[K+].O>CS(C)=O>[C:28]([CH2:11][C:12]([CH3:25])([CH3:26])[CH2:13][O:14][S:15]([C:18]1[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=1)(=[O:16])=[O:17])#[N:29]

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 2642531,3-Bis(tosyloxy)-2,2-dimethylpropane

Product 1

HCID 323833HCID 323833, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of toluene-4-sulfonic acid 3-toluene-4-sulfonyloxy-2,2-dimethylpropyl ester (5.0 g, 12.1 mmol) in DMSO (15 mL) is added KCN (789 mg, 12.1 mmol). The mixture is stirred at 80° C. for 18 h then cooled to RT. The mixture is poured into water and extracted with ether. The organic layer is dried over sodium sulfate the filtrate concentrated. The crude material is purified by column chromatography to give the title compound.

Workup

  1. temperaturethen cooled to RT
  2. extractionextracted with ether
  3. dry with materialThe organic layer is dried over sodium sulfate the filtrate
  4. concentrationconcentrated
  5. customThe crude material is purified by column chromatography

Sources & evidence

ORD record
ord-23a048d5281142318617d81f4b51af15
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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