Pentanoic acid, 2-acetyl-, ethyl ester → HCID 178439771, compound

HRID 2081573Notes

Reaction equation

HRID 2081573 reaction equation
[CH2:1]([CH:4]([C:10]([CH3:12])=O)[C:5]([O:7]CC)=O)[CH2:2][CH3:3].[F:13][C:14]([F:19])([F:18])[C:15]([NH2:17])=[NH:16].[O-][CH2:21]C.[Na+]>C(O)C>[OH:7][C:5]1[C:4]([CH2:10][CH2:12][CH3:21])=[C:1]([CH2:2][CH3:3])[N:17]=[C:15]([C:14]([F:19])([F:18])[F:13])[N:16]=1

Participants

5

Reactant 3

HCID 95398Pentanoic acid, 2-acetyl-, ethyl esterHCID 2723922Sodium ethoxideHCID 2776882Trifluoroacetamidine

Product 1

HCID 178439771HCID 178439771, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 2-n-propylacetoacetate (0.5 mole), trifluoroacetamidine (0.67 mole) and sodium ethoxide (1 mole) in ethanol was heated at reflux temperature overnight and then evaporated to dryness. The residue was triturated in water and acidified with glacial acetic acid to yield the title compound. TLC, Silica gel (cyclohexane-ethyl acetate, 1:1) Rf 0.80 1H NMR (CDCl3): δ 0.95 (t,3H) 1.25 (t,3H) 1.57 (m,2H) 2.58 (q,2H) 2.70 (q,2H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature overnight
  3. customevaporated to dryness
  4. customThe residue was triturated in water

Sources & evidence

ORD record
ord-f6404edd30a74f508b421e758dd51573
Source dataset
uspto-grants-1993_02
Patent number
US05185340

Reaction notes

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