Chloromethyl Methyl Ether → HCID 18182399, compound

HRID 1359276Notes

Reaction equation

HRID 1359276 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([C:14]1[C:19]([OH:20])=[CH:18][CH:17]=[C:16]([CH2:21][O:22][Si](C(C)(C)C)(C)C)[N:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:30][O:31][CH2:32]Cl.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O.CN(C)C=O>[CH2:7]([C:14]1[C:19]([O:20][CH2:30][O:31][CH3:32])=[CH:18][CH:17]=[C:16]([CH2:21][OH:22])[N:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 2724141Tetrabutylammonium FluorideHCID 18182288HCID 18182288, compound

Product 1

HCID 18182399HCID 18182399, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

63 g of potassium carbonate and 300 ml of N,N-dimethylformamide were added to 100 g of 2-benzyl-6-(tert-butyldimethylsilyl)oxymethyl-3-hydroxypyridine and 23 ml of chloromethyl methyl ether was added dropwise into the mixture at room temperature under stirring using a mechanical stirrer. After heating under stirring at 50° C. for 2 hours in an oil bath, water was added thereto and the mixture was extracted with ethyl acetate. Further, the organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and the solvent was removed. The resulting residue was dissolved by adding 400 ml of tetrahydrofuran and 300 ml of a tetrahydrofuran solution containing 1 mol of tetra-n-butylammonium fluoride was added thereto under ice-cooling. After stirring under ice-cooling, water was added thereto and the mixture was extracted with ethyl acetate. Further, the organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and evaporated. The residue was dissolved in 50% ethyl acetate/hexane and filtered through silica gel. The filtrate was evaporated and dried, to give 73 g of the target compound.

Workup

  1. additionwas added dropwise into the mixture at room temperature
  2. temperatureAfter heating
  3. stirringunder stirring at 50° C. for 2 hours in an oil bath
  4. extractionthe mixture was extracted with ethyl acetate
  5. washFurther, the organic phase was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed
  8. dissolutionThe resulting residue was dissolved
  9. additionby adding 400 ml of tetrahydrofuran and 300 ml of a tetrahydrofuran solution
  10. additionwas added
  11. temperatureunder ice-cooling
  12. stirringAfter stirring under ice-
  13. temperaturecooling
  14. extractionthe mixture was extracted with ethyl acetate
  15. washFurther, the organic phase was washed with water and brine
  16. dry with materialdried over anhydrous magnesium sulfate
  17. customevaporated
  18. dissolutionThe residue was dissolved in 50% ethyl acetate/hexane
  19. filtrationfiltered through silica gel
  20. customThe filtrate was evaporated
  21. customdried

Sources & evidence

ORD record
ord-a3e596525f2d4cb292f1db8034bf3a3a
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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