Methyl acetoacetate → HCID 18673606, compound

HRID 1635944Notes

Reaction equation

HRID 1635944 reaction equation
O=[C:2]([CH3:8])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[N+:9](/[CH:12]=[CH:13]/[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)([O-])=O.C[O-].[Na+].C(OC(=O)C)C.CCCCCC>CO.N>[CH3:7][O:6][C:4]([C:3]1[C:13]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)=[CH:12][NH:9][C:2]=1[CH3:8])=[O:5]

Participants

7

Reactant 4

HCID 7757Methyl acetoacetateHCID 538167937630-26-5HCID 10942334Sodium MethoxideHCID 21226206Ethyl acetate hexane

Product 1

HCID 18673606HCID 18673606, compoundYield 59.8%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

0.69 g(5.9 mmol) of methyl 3-oxobutanoate and 1.08 g(5.9 mmol) of 1-[(E)-2-nitroethenyl]naphthalene were added to 2.37 ml of 0.5M sodium methoxide in methanol, and the resulting mixture was stirred for 2 hours at 0° C. The reaction solution was diluted with 10 ml of cold methanol, through which ammonia gas was passed. Reaction was carried out for 12 hours at 0° C. under stirring. After reaction was completed, the solvent was removed under reduced pressure and the residue was subjected to column chromatography(eluent: ethylacetate/hexane=90/10, v/v; ethylacetate/hexane=70/30, v/v) to give 936 mg(3.53 mmol, Yield 59%) of the title compound.

Workup

  1. customReaction
  2. waitwas carried out for 12 hours at 0° C.
  3. stirringunder stirring
  4. customAfter reaction
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8b76108161264c74b3b2199b8efe58cd
Source dataset
uspto-grants-2003_01
Patent number
US06511978B1

Reaction notes

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