Methyl acetoacetate → HCID 86714189, compound

HRID 1411086Notes

Reaction equation

HRID 1411086 reaction equation
[CH2:1]([CH:3]([CH2:6][CH3:7])[CH2:4][NH2:5])[CH3:2].[CH3:8][O:9][C:10](=[O:15])[CH2:11][C:12](=O)[CH3:13].[CH3:16][O:17][C:18](=[O:21])[C:19]#[CH:20]>CO>[CH3:16][O:17][C:18](=[O:21])[CH:19]=[CH:20][C:11](=[C:12]([NH:5][CH2:4][CH:3]([CH2:6][CH3:7])[CH2:1][CH3:2])[CH3:13])[C:10]([O:9][CH3:8])=[O:15]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 120492-Ethyl butylamineHCID 13536Methyl propiolate

Product 1

HCID 86714189HCID 86714189, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-ethyl-butylamine (4.5 g, 44.6 mmol) and 3-oxo-butyric acid methyl ester (5.8 mL, 53.5 mmol) in MeOH (170 mL) was refluxed for 2 h. Propynoic acid methyl ester (6 mL, 66.8 mmol) was added, and the resulting mixture was refluxed for 2 days. After cooling to r.t., the solvent was evaporated. The residue was purified by silica gel chromatography (0-30% EtOAc/hexanes) to give 7.32 g of the title compound as an orange oil. MS: (+) m/z 284.35 (M+1).

Workup

  1. temperaturewas refluxed for 2 h
  2. temperaturethe resulting mixture was refluxed for 2 days
  3. customthe solvent was evaporated
  4. customThe residue was purified by silica gel chromatography (0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a4d270fab985496b84d9b7d1f6ab92ad
Source dataset
uspto-grants-2014_12
Patent number
US08921389B2

Reaction notes

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