Acetic Anhydride → HCID 23369584, compound

HRID 1900797Notes

Reaction equation

HRID 1900797 reaction equation
[OH:1][CH2:2][CH:3]([C:6]1[C:7]([OH:18])=[C:8]2[C:13](=[C:14]([CH3:16])[CH:15]=1)[NH:12][C:11](=[O:17])[CH:10]=[CH:9]2)[CH:4]=[CH2:5].[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].[C:27](OC(=O)C)(=[O:29])[CH3:28]>N1C=CC=CC=1>[C:27]([O:18][C:7]1[C:6]([CH:3]([CH2:2][O:1][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH:4]=[CH2:5])=[CH:15][C:14]([CH3:16])=[C:13]2[C:8]=1[CH:9]=[CH:10][C:11](=[O:17])[NH:12]2)(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 23369638HCID 23369638, compound

Product 1

HCID 23369584HCID 23369584, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

6-(1-Hydroxymethyl-2-propenyl)-5-hydroxy-8-methylcarbostyril (8.40 g, 34.3 mmol) was dissolved in pyridine (120 ml), to which tert-butyldimethylsilylchloride (7.5 g, 49.8 mmol) was added. The mixture was stirred at room temperature for 3 hours. Acetic anhydride (20 ml, 0.212 mol) was added to the reaction mixture, followed by stirring at room temperature for 90 minutes, then condensing under reduced pressure. The resultant residue was subjected to an azeotropic distillation along with toluene. The residue was extracted from chloroform--1N-HCl. The organic phase was washed with saturated aqueous NaCl solution, dried, and condensed under reduced pressure. The residue was purified by silica gel chromatography (chloroform: ether=1:1), and then the obtained crude crystals was recrystallized from chloroform--n-hexane. As a result, 6.00 g of the title compound was obtained as colorless powdery crystals (43.6%).

Workup

  1. additionwas added
  2. stirringby stirring at room temperature for 90 minutes
  3. customcondensing under reduced pressure
  4. distillationThe resultant residue was subjected to an azeotropic distillation along with toluene
  5. extractionThe residue was extracted from chloroform--1N-HCl
  6. washThe organic phase was washed with saturated aqueous NaCl solution
  7. customdried
  8. customcondensed under reduced pressure
  9. customThe residue was purified by silica gel chromatography (chloroform: ether=1:1)
  10. customthe obtained crude crystals
  11. customwas recrystallized from chloroform

Sources & evidence

ORD record
ord-73845daad11f4bdebe1719b463000d4d
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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