Butanoic acid, 2-acetyl-3-methyl-, ethyl ester → HCID 136043553, compound

HRID 1742022Notes

Reaction equation

HRID 1742022 reaction equation
[CH:1]([CH:4]([C:10]([CH3:12])=O)[C:5]([O:7]CC)=O)([CH3:3])[CH3:2].[F:13][C:14]([F:19])([F:18])[C:15]([NH2:17])=[NH:16].O(C)[Na]>CO>[CH3:12][C:10]1[N:16]=[C:15]([C:14]([F:19])([F:18])[F:13])[NH:17][C:5](=[O:7])[C:4]=1[CH:1]([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 95544Butanoic acid, 2-acetyl-3-methyl-, ethyl esterHCID 2776882TrifluoroacetamidineHCID 178418582HCID 178418582, compound

Product 1

HCID 136043553HCID 136043553, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2-isopropylacetoacetate (35.8 mL, 0.2 mol) was mixed with trifluoroacetamidine (23 g, 0.2 mol) in MeOH, and then NaOCH3 (21.6 g, 0.4 mol) was added. The mixture was refluxed for 18 h then evaporated to dryness. The residue was taken up in H2O (200 mL) and extracted with ether. The aqueous solution was reduced in volume and acidified with acetic acid to pH 5 then extracted with EtOAc. The combined organic extracts were washed with a small quantity of water, dried over Na2SO4, then evaporated to afford 28 g of an oil. The crude product was purified by flash chromatography (CHCl3) to provide 16 g (36% yield) of pure compound.

Workup

  1. temperatureThe mixture was refluxed for 18 h
  2. customthen evaporated to dryness
  3. extractionextracted with ether
  4. extractionthen extracted with EtOAc
  5. washThe combined organic extracts were washed with a small quantity of water
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-93f58cd3d0464d87abbd67e48266252d
Source dataset
uspto-grants-1994_08
Patent number
US05336677

Reaction notes

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