Hydrochloric Acid → 4-Ethyl-2-hydroxyimino-5-nitro-3-hexen-1-ol

HRID 35584Notes

Reaction equation

HRID 35584 reaction equation
[CH2:1]([C:3]([CH:10]([N+:12]([O-:14])=[O:13])[CH3:11])=[CH:4][C:5](=[N:8][OH:9])[CH:6]=[O:7])[CH3:2].[BH4-].[Na+].Cl>C(O)C>[CH2:1]([C:3]([CH:10]([N+:12]([O-:14])=[O:13])[CH3:11])=[CH:4][C:5](=[N:8][OH:9])[CH2:6][OH:7])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 86257292HCID 86257292, compound

Product 1

HCID 862573024-Ethyl-2-hydroxyimino-5-nitro-3-hexen-1-olYield 79.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-ethyl-2-hydroxyimino-5-nitro-3-hexenal (100 mg) in dry ethanol (10 ml) was added sodium borohydride (15 mg) at 0° C. with stirring. The resulting mixture was stirred at the same temperature for 10 minutes and 1N hydrochloric acid was added thereto. The reaction mixture was extracted with ethyl acetate and the extract was washed with successively with water, an aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate, and then evaporated to dryness in vacuo to give an oil. The oil was purified by a preparative thin layer chromatography [solvent: methanol-chloroform (10:90) to give 4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-ol (80 mg).

Workup

  1. stirringThe resulting mixture was stirred at the same temperature for 10 minutes
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washthe extract was washed with successively with water
  4. dry with materialan aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate
  5. customevaporated to dryness in vacuo
  6. customto give an oil
  7. customThe oil was purified by a preparative thin layer chromatography [solvent

Sources & evidence

ORD record
ord-1ee4a9c866574849a843d4122565d74c
Source dataset
uspto-grants-1988_08
Patent number
US04767768

Reaction notes

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