Dimethylformamide dimethyl acetal → HCID 54519109, compound

HRID 1094804Notes

Reaction equation

HRID 1094804 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH2:4][C:5]([CH2:7][O:8][CH3:9])=[O:6].CO[CH:13](OC)[N:14]([CH3:16])[CH3:15]>CCCCCCC>[CH3:13][N:14]([CH:16]=[C:4]([C:5](=[O:6])[CH2:7][O:8][CH3:9])[C:3]([O:2][CH3:1])=[O:10])[CH3:15]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 123500Methyl 4-methoxyacetoacetate

Product 1

HCID 54519109HCID 54519109, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
90 °C

Procedure

Methyl-4-methoxyacetoacetate (9 ml, 70 mmol) was added to dimethylformamide dimethylacetal (18.8 ml, 139 mmol) and the reaction stirred at 90° C. for 2 hours before cooling to room temperature and stirring for 18 hours. The reaction was concentrated in vacuo and purified by silica gel column chromatography, eluting with 70:30 to 100:0 ethyl acetate:heptane to afford the title compound as an oil (7.68 g, 50% yield).

Workup

  1. temperaturebefore cooling to room temperature
  2. stirringstirring for 18 hours
  3. concentrationThe reaction was concentrated in vacuo
  4. custompurified by silica gel column chromatography
  5. washeluting with 70:30 to 100:0 ethyl acetate

Sources & evidence

ORD record
ord-63f6c3b04652445f8c49979208e7039c
Source dataset
uspto-grants-2012_03
Patent number
US08134007B2

Reaction notes

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