Methyl acetoacetate → HCID 13552997, compound

HRID 745527Notes

Reaction equation

HRID 745527 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]=O.[C:14]([O:20][CH3:21])(=[O:19])[CH2:15][C:16]([CH3:18])=O.[OH-:22].[NH4+:23]>CO>[CH3:18][C:16]1[NH:23][C:16]([CH3:18])=[C:15]([C:14]([O:20][CH3:21])=[O:22])[CH:8]([C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[C:15]=1[C:14]([O:20][CH3:21])=[O:19]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 14923Ammonium HydroxideHCID 27955582-(Thiophen-2-yl)benzaldehyde

Product 1

HCID 13552997HCID 13552997, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Compound 1a (0.5 mmol) in methanol (5 mL) was added methyl acetoacetate (1.0 mmol) and concentrated ammonium hydroxide (1.0 mmol) and the reaction mixture was refluxed for 4 days. The solvent was removed in vacuo and the residue purified by flash chromatography on silica gel eluted with diethyl ether:hexane (1:1) and trituration with diethyl ether:hexane (1:2) to afford Compound 1b as a white solid (m.p. 173°-175° C.).

Workup

  1. temperaturethe reaction mixture was refluxed for 4 days
  2. customThe solvent was removed in vacuo
  3. customthe residue purified by flash chromatography on silica gel
  4. washeluted with diethyl ether:hexane (1:1) and trituration with diethyl ether:hexane (1:2)

Sources & evidence

ORD record
ord-0613ccf2c2fd413aa6499a9fda6935e9
Source dataset
uspto-grants-1986_07
Patent number
US04599341

Reaction notes

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