Ethyl Acetate → HCID 178427780, compound

HRID 986784Notes

Reaction equation

HRID 986784 reaction equation
[O:1]=[C:2]([CH2:11][O:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[N:23]([O-])=[O:24].[Na+].C(OCC)(=O)C>C(O)(=O)C>[OH:24][N:23]=[C:3]([C:2](=[O:1])[CH2:11][O:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 13390692HCID 13390692, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 178427780HCID 178427780, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4.5 g of t-butyl 3-oxo-4-p-toluenesulphonyloxybutyrate were dissolved in 40 ml of acetic acid, and then 1.42 g of sodium nitrite were added, at room temperature, to the solution over a period of 10 minutes. The mixture was then stirred at room temperature for 50 minutes, after which 200 ml of ethyl acetate were added and the mixture was then washed with an aqueous solution of sodium chloride. The ethyl acetate solution was dried over magnesium sulphate and, after filtering off the drying agent, the filtrate was concentrated by evaporation under reduced pressure to give a brown, oily substance. This oily substance was purified by column chromatography through silica gel, eluted with a 4:1 by volume mixture of cyclohexane and ethyl acetate, affording 1.66 g of t-butyl 2-hydroxyimino-3-oxo-4-p-toluenesulphonyloxybutyrate, in the form of colourless crystals, melting at 106°-108° C. (with decomposition, recrystallized from a 1:1 by volume mixture of diethyl ether and petroleum ether).

Workup

  1. washthe mixture was then washed with an aqueous solution of sodium chloride
  2. dry with materialThe ethyl acetate solution was dried over magnesium sulphate
  3. filtrationafter filtering off the drying agent
  4. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  5. customto give a brown, oily substance
  6. customThis oily substance was purified by column chromatography through silica gel
  7. washeluted with a 4:1 by volume mixture of cyclohexane and ethyl acetate

Sources & evidence

ORD record
ord-2d89e98104c24836b991e99a6dbd4d29
Source dataset
uspto-grants-1987_12
Patent number
US04716158

Reaction notes

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