Methanol → HCID 74952549, compound

HRID 1587753Notes

Reaction equation

HRID 1587753 reaction equation
[CH3:1][O:2][N+:3]([O-])=[C:4]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[CH3:5].[B].[H-].[Na+].C[OH:17]>>[CH3:1][O:2][N:3]=[C:4]([C:6]1[CH2:7][N:8]([OH:17])[CH2:9][CH2:10][CH:11]=1)[CH3:5]

Participants

5

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 5462311BoronHCID 86746957HCID 86746957, compound

Product 1

HCID 74952549HCID 74952549, compound

Conditions

Temperature
-10 °C

Procedure

3.5 g of 3-acetyl-pyridine-O-methyl-oxime-N-oxide [J. Heterocyclic Chem. 16 1459, (1979)] is dissolved in 50 cm3 of methanol and cooled to -10° C. 2.4 g of boron and sodium hydride is added, with agitation for 2 hours at ambient temperature followed by evaporation to dryness. The residue is taken up with water and extracted with ethyl acetate. The extracts are dried, evaporated to dryness, and purified by chromatography on silica gel, (eluene: ethyl acetate). 2.85 g of the expected product is obtained. m.p. 94°-96° C., after crystallizing from hexane.

Workup

  1. customfollowed by evaporation to dryness
  2. extractionextracted with ethyl acetate
  3. customThe extracts are dried
  4. customevaporated to dryness
  5. custompurified by chromatography on silica gel, (eluene: ethyl acetate)

Sources & evidence

ORD record
ord-861c18133dc7447884794f5cb4b22646
Source dataset
uspto-grants-1993_06
Patent number
US05219873

Reaction notes

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