Acetic Anhydride → HCID 23325041, compound

HRID 1732616Notes

Reaction equation

HRID 1732616 reaction equation
[N:1]([O-])=O.[Na+].[C:5]([CH:11](C(C)=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[O:10])[CH2:6][CH2:7][CH2:8][CH3:9].[C:20](Cl)(=[O:25])[CH2:21]CCC.C(OC(=O)C)(=O)C>O.C(O)(=O)C.[Zn]>[CH2:15]([O:14][C:12](=[O:13])[CH:11]([NH:1][C:20](=[O:25])[CH3:21])[C:5](=[O:10])[CH2:6][CH2:7][CH2:8][CH3:9])[CH3:16]

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 61186Valeryl chlorideHCID 12688297HCID 12688297, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 23325041HCID 23325041, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of sodium nitrite (41.3g) in water was added slowly to a cooled solution of ethyl 2-valerylacetoacetate (118.7g) in acetic acid (100 ml.), and the temperature was kept below 10°. Ice (100g) was added, followed by acetic anhydride (105.0g). Zinc dust (total 65.4g) was added portionwise, keeping the temperature below 20° with stirring, until the reaction was complete. The mixture was allowed to stand overnight at room temperature, and it was then filtered. The solid was washed wih chloroform, and the filtrate was extracted with chloroform. The chloroform extracts were washed with sodium carbonate solution and dried. The solvent was removed under vacuum, and the residue was purified by column chromatography (silica gel) eluting with petroleum ether (b.p. 60-80°)/ethyl acetate, to yield ethyl-2-acetamido-3-oxoheptanoate, 13.5g, which was used without further purification.

Workup

  1. customwas kept below 10°
  2. customthe temperature below 20°
  3. filtrationit was then filtered
  4. washThe solid was washed wih chloroform
  5. extractionthe filtrate was extracted with chloroform
  6. washThe chloroform extracts were washed with sodium carbonate solution
  7. customdried
  8. customThe solvent was removed under vacuum
  9. customthe residue was purified by column chromatography (silica gel)
  10. washeluting with petroleum ether (b.p. 60-80°)/ethyl acetate

Sources & evidence

ORD record
ord-66bc7d072e8a43feadfe8a478acf0ee0
Source dataset
uspto-grants-1980_12
Patent number
US04238494

Reaction notes

Loading…