p-Toluenesulfonic acid → HCID 66975468, compound

HRID 1022639Notes

Reaction equation

HRID 1022639 reaction equation
[Si]([O:8][CH2:9][CH:10]([OH:22])[CH:11]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1)[C:12]#[N:13])(C(C)(C)C)(C)C.CO[C:25](OC)([CH3:27])[CH3:26].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Cl:21][C:16]1[CH:15]=[C:14]([CH:11]([CH:10]2[CH2:9][O:8][C:25]([CH3:27])([CH3:26])[O:22]2)[C:12]#[N:13])[CH:19]=[CH:18][C:17]=1[Cl:20]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 516892Sodium BicarbonateHCID 66975505HCID 66975505, compound

Product 1

HCID 66975468HCID 66975468, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (2RS,3RS)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,4-dichlorophenyl)-3-hydroxybutanenitrile (152 g) in toluene (1000 ml) were added 2,2-dimethoxypropane (131.8 g) and p-toluenesulfonic acid (8.02 g), and the mixture was stirred under nitrogen purging at 80° C. for 2 hr. Under ice-cooling, the mixture was neutralized with saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was crystallized from diisopropyl ether to give the title compound (99 g) as colorless crystals.

Workup

  1. temperatureUnder ice-cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-6433c75e7cd44abaa94e0f6d4ab85bfb
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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