Sodium Sulfite → HCID 23369571, compound

HRID 1900798Notes

Reaction equation

HRID 1900798 reaction equation
[C:1]([O:4][C:5]1[C:14]([CH:15]([CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH:16]=[CH2:17])=[CH:13][C:12]([CH3:27])=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:28])[NH:10]2)(=[O:3])[CH3:2].S([O-])([O-])=[O:30].[Na+].[Na+]>C(Cl)(Cl)Cl>[C:1]([O:4][C:5]1[C:14]([CH:15]([CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH:16]2[O:30][CH2:17]2)=[CH:13][C:12]([CH3:27])=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:28])[NH:10]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24437Sodium SulfiteHCID 23369584HCID 23369584, compound

Product 1

HCID 23369571HCID 23369571, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5-Acetoxy-6-[1-(tert-butyldimethylsilyloxy)methyl-2propenyl]-8-methylcarbostyril (6.00 g, 15.0 mmol) was dissolved in chloroform (100 ml), to which m-perbenzoic acid (13.0 g, 52.7 mmol) was added. The mixture was stirred for hours. Saturated aqueous sodium sulfite solution was added to the reaction mixture, followed by stirring for 90 minutes. The organic phase was washed with saturated NaCl solution, dried over sodium sulfate and condensed under reduced pressure. The resultant residue was recrystallized from chloroform--n-hexane. As a result, 6.10 g of the title compound (mixtures of diastereomers, 3:1) was obtained as colorless powdery crystals (97.8%).

Workup

  1. additionwas added
  2. stirringby stirring for 90 minutes
  3. washThe organic phase was washed with saturated NaCl solution
  4. dry with materialdried over sodium sulfate and condensed under reduced pressure
  5. customThe resultant residue was recrystallized from chloroform

Sources & evidence

ORD record
ord-989894664edb41029c612f9b9f017ca6
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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