Pyridine → HCID 19699952, compound

HRID 863201Notes

Reaction equation

HRID 863201 reaction equation
C(OC(=O)C)(=O)C.O[CH:9]([C:22]1[CH:27]=[CH:26][C:25]([CH:28]2OCCO2)=[CH:24][CH:23]=1)[C:10]1[CH:15]=[CH:14][C:13]([CH:16]([O:18]COC)[CH3:17])=[CH:12][CH:11]=1.[H][H].[N:35]1C=CC=C[CH:36]=1>[Pd].C(O)C.O>[CH3:36][NH:35][CH2:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]([OH:18])[CH3:17])=[CH:12][CH:11]=2)=[CH:23][CH:24]=1

Participants

8

Reactant 4

HCID 1049Pyridine2×HCID 7918Acetic AnhydrideHCID 19699937HCID 19699937, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19699952HCID 19699952, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

20 ml of acetic anhydride was dropwise added to a comprising 22.8 g of the 2-[4-[α-hydroxy-4-(1-methoxymethyloxyethyl)benzyl]phenyl]-1,3-dioxolane prepared in the step (a) and 30 ml of pyridine, and the obtained mixture was stirred at room temperature for 3 hours. After the completion of the reaction, 10 ml of water was added to the reaction mixture and the obtained mixture was further stirred for 30 minutes and poured onto ice-water. The resulting mixture was extracted with ethyl acetate. The organic phase was washed with 1N hydrochloric acid, water, an aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of common salt successively, dried and distilled to remove the solvent, giving a colorless oil. 2 ml of pyridine, 100 ml of ethanol and 3 g of palladium/carbon were added to the oil and the obtained mixture was stirred in a hydrogen atmosphere at room temperature for 3 hours. After the completion of the reaction, the reaction mixture was filtered and the filtrate was subjected to vacuum distillation to remove the solvent. The residue was purified by silica gel column chromatography [hexane/ethyl acetate (85:15)] to give 21 g of the title compound.

Workup

  1. additionwas added to the reaction mixture
  2. stirringthe obtained mixture was further stirred for 30 minutes
  3. additionpoured onto ice-water
  4. extractionThe resulting mixture was extracted with ethyl acetate
  5. washThe organic phase was washed with 1N hydrochloric acid, water
  6. dry with materialan aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of common salt successively, dried
  7. distillationdistilled
  8. customto remove the solvent
  9. customgiving a colorless oil
  10. customAfter the completion of the reaction
  11. filtrationthe reaction mixture was filtered
  12. distillationthe filtrate was subjected to vacuum distillation
  13. customto remove the solvent
  14. customThe residue was purified by silica gel column chromatography [hexane/ethyl acetate (85:15)]

Sources & evidence

ORD record
ord-09eb67646c904c19a0ae296bab49c86c
Source dataset
uspto-grants-1998_02
Patent number
US05719303

Reaction notes

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