Acetic Acid → Benzyl 3-(methylamino)but-2-enoate

HRID 82309Notes

Reaction equation

HRID 82309 reaction equation
[C:1]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:6])[CH2:2][C:3]([CH3:5])=O.[NH2:15][CH3:16].C(O)(=O)C.[O-]S([O-])(=O)=O.[Mg+2]>CO.CCOC(C)=O>[CH3:16][NH:15][C:3]([CH3:5])=[CH:2][C:1]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6329MethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 142266Benzyl acetoacetate

Product 1

HCID 66660284Benzyl 3-(methylamino)but-2-enoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyl acetoacetate (57.6 g, 300 mmol) in MeOH (50 mL) in a 350 mL pressure vessel was added H2NMe (150 mL of a 2M solution in MeOH, 300 mmol) and acetic acid (2 mL). The capped vessel was placed in an oil bath at 70° C. and the reaction mixture was stirred for 16 hours. After the mixture had cooled to room temperature, the solvent was evaporated in vacuo leaving a yellow emulsion, which was dissolved in EtOAc (500 mL) and MgSO4 was added to remove water. The drying agent was filtered off, and the solvent evaporated in vacuo to give benzyl 3-(Methylamino)but-2-enoate as a viscous yellow oil in quantitative yield 60 g which was used without further purification.

Workup

  1. customThe capped vessel was placed in an oil bath at 70° C.
  2. customthe solvent was evaporated in vacuo
  3. customleaving a yellow emulsion, which
  4. customto remove water
  5. filtrationThe drying agent was filtered off
  6. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-5b8288988b05477790a57d599e193414
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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