Methanol → HCID 54200213, compound

HRID 1981165Notes

Reaction equation

HRID 1981165 reaction equation
[BH4-].[Na+].CO.[Cl:5][C:6]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:7]=1[O:8][C:9]([C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1>C(OCC)(=O)C>[Cl:5][C:6]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:7]=1[O:8][C:9]([CH:17]([OH:22])[C:18]([CH3:20])([CH3:21])[CH3:19])=[CH:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 54142624HCID 54142624, compound

Product 1

HCID 54200213HCID 54200213, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In this example, 0.49 g (0.0129 mole) of sodium borohydride was added portion-wise to a mixture containing 20 ml of methanol and 4.5 g (0.0129 mole) of 3-[2-(2,4-dichlorophenoxy)-3-oxo-4,4-dimethylpent-1-enyl]pyridine at 0° C. with stirring. The mixture was stirred at 0° C. for 15 minutes, then quenched by the addition of water. The mixture was then diluted with more water and then extracted twice with methylene chloride. The methylene chloride extracts were washed with water twice, dried over magnesium sulfate, filtered, then concentrated under vacuum affording a foam. The foam was dissolved in ethyl acetate, then chromatographed by flash column chromatography (silica gel) eluting with hexane and ethyl acetate mixtures. The product fractions were combined, concentrated and the residue recrystallized from methanol and water affording white crystals of the title compound mp 79.0°-81.5° C.

Workup

  1. stirringThe mixture was stirred at 0° C. for 15 minutes
  2. customquenched by the addition of water
  3. additionThe mixture was then diluted with more water
  4. extractionextracted twice with methylene chloride
  5. washThe methylene chloride extracts were washed with water twice
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customaffording a foam
  10. customchromatographed by flash column chromatography (silica gel)
  11. washeluting with hexane and ethyl acetate mixtures
  12. concentrationconcentrated
  13. customthe residue recrystallized from methanol and water affording white crystals of the title compound mp 79.0°-81.5° C.

Sources & evidence

ORD record
ord-e2492f9ed0b345828c42f29fa96c9dfb
Source dataset
uspto-grants-1985_04
Patent number
US04512995

Reaction notes

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