Dimethylformamide → HCID 19418544, compound

HRID 1734947Notes

Reaction equation

HRID 1734947 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[C:20]([OH:21])=[C:19]([O:22][CH3:23])[C:18]([O:24][CH3:25])=[C:17]([O:26][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[C:16]=1[CH3:44])(=O)C.Cl.[Cl:46][CH2:47][C:48]1[CH:53]=[CH:52][N:51]=[CH:50][CH:49]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[ClH:46].[CH3:23][O:22][C:19]1[C:18]([O:24][CH3:25])=[C:17]([OH:26])[C:16]([CH3:44])=[C:15]([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][OH:4])[C:20]=1[O:21][CH2:47][C:48]1[CH:53]=[CH:52][N:51]=[CH:50][CH:49]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 745704-(Chloromethyl)pyridinium chlorideHCID 152949946-(10-Acetoxydecyl)-4-tert-butyldiphenylsilyloxy-2,3-dimethoxy-5-methylphenol

Product 1

HCID 19418544HCID 19418544, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-(10-acetoxydecyl)-4-tert-butyldiphenylsilyloxy-2,3-dimethoxy-5-methylphenol (3.70 g) obtained in Example B-1, 4-chloromethylpyridine hydrochloride (1.96 g), potassium carbonate (5.00 g) and dimethylformamide (30 ml) was stirred at room temperature for 16 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was dissolved in tetrahydrofuran (30 ml). Tetrabutylammonium fluoride trihydrate (1 g) was added, and the mixture was stirred at room temperature for 1 hour. The mixture was concentrated under reduced pressure. Methanol (50 ml) and 1N sodium hydroxide solution (10 ml) were added to the residue, and the mixture was stirred at room temperature for 16 hours. After concentration, the residue was subjected to column chromatography on silica gel and eluted with ethyl acetate. The desired fraction was concentrated. The residue was dissolved in ethanol (30 ml), and conc. hydrochloric acid (0.7 ml) was added. The crystals obtained after concentration under reduced pressure were separated by filtration and washed with ether to obtain the desired compound (1.2 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in tetrahydrofuran (30 ml)
  4. additionTetrabutylammonium fluoride trihydrate (1 g) was added
  5. stirringthe mixture was stirred at room temperature for 1 hour
  6. concentrationThe mixture was concentrated under reduced pressure
  7. additionMethanol (50 ml) and 1N sodium hydroxide solution (10 ml) were added to the residue
  8. stirringthe mixture was stirred at room temperature for 16 hours
  9. concentrationAfter concentration
  10. washeluted with ethyl acetate
  11. concentrationThe desired fraction was concentrated
  12. dissolutionThe residue was dissolved in ethanol (30 ml)
  13. additionconc. hydrochloric acid (0.7 ml) was added
  14. customThe crystals obtained
  15. concentrationafter concentration under reduced pressure
  16. customwere separated by filtration
  17. washwashed with ether

Sources & evidence

ORD record
ord-54aeaa4f048644558c6bde2abd952d3b
Source dataset
uspto-grants-1996_07
Patent number
US05534639

Reaction notes

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