Potassium Carbonate → Methyl 4-methoxy-2-(1-methylacetonyl)-acetoacetate

HRID 329804Notes

Reaction equation

HRID 329804 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][CH2:9][C:10](=[O:16])[CH2:11][C:12]([O:14][CH3:15])=[O:13].Cl[CH:18]([CH3:22])[C:19](=[O:21])[CH3:20]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(#N)C>[CH3:7][O:8][CH2:9][C:10](=[O:16])[CH:11]([CH:18]([CH3:22])[C:19]([CH3:20])=[O:21])[C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 200263-Chloro-2-butanoneHCID 123500Methyl 4-methoxyacetoacetate

Product 1

HCID 19871668Methyl 4-methoxy-2-(1-methylacetonyl)-acetoacetateYield 42%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

16.58 g (120 mmol) of potassium carbonate and 0.46 g (2 mmol) of benzyltriethylammonium chloride are suspended in 50 ml of acetonitrile. While stirring there are added thereto 14.60 g (100 mmol) of methyl 4-methoxyacetoacetate and there are added dropwise thereto within 10 minutes 15.97 g (150 mmol) of 3-chloro-2-butanone. The mixture is stirred at 20°-25° C. for a further 65 hours. The reaction mixture is poured on to 70 ml of 4N HCl/ice (pH value=1) and extracted 3 times with 100 ml of ethyl acetate each time. The combined organic phases are dried over magnesium sulphate and concentrated on a rotary evaporator. The crude product distils at 95° C./0.05 mbar and gives 6.67 g (42%) of methyl 4-methoxy-2-[1-methylacetonyl]-acetoacetate.

Workup

  1. additionare added
  2. stirringThe mixture is stirred at 20°-25° C. for a further 65 hours
  3. extractionextracted 3 times with 100 ml of ethyl acetate each time
  4. dry with materialThe combined organic phases are dried over magnesium sulphate
  5. concentrationconcentrated on a rotary evaporator
  6. customThe crude product distils at 95° C./0.05 mbar

Sources & evidence

ORD record
ord-411e00c5ef8d4e01915a38867e01c4ac
Source dataset
uspto-grants-1990_01
Patent number
US04892966

Reaction notes

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