Sodium ethoxide → HCID 68515283, compound

HRID 1717427Notes

Reaction equation

HRID 1717427 reaction equation
[N:1]([C:4]1[CH:17]=[CH:16][C:7]([C:8]([NH:10][CH2:11][C:12]([F:15])([F:14])[F:13])=[O:9])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].O=[C:19]([CH2:26][CH:27]=[CH2:28])[CH2:20][C:21]([O:23]CC)=[O:22].[O-]CC.[Na+]>C(O)C>[CH:26](/[C:19]1[N:1]([C:4]2[CH:5]=[CH:6][C:7]([C:8]([NH:10][CH2:11][C:12]([F:14])([F:13])[F:15])=[O:9])=[CH:16][CH:17]=2)[N:2]=[N:3][C:20]=1[C:21]([OH:23])=[O:22])=[CH:27]\[CH3:28]

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 14110565Ethyl 3-oxohex-5-enoateHCID 86629793HCID 86629793, compound

Product 1

HCID 68515283HCID 68515283, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 4-azido-N-(2,2,2-trifluoroethyl)benzamide (2.44 g) obtained in Example 46a) in ethanol (40 ml) were added ethyl 3-oxohex-5-enoate (Tetrahedron Lett., 41, 8803-8806 (2000)) (2.10 g) synthesized separately and 20% sodium ethoxide in ethanol solution (4.6 ml), and the mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, and the residue was diluted with water and washed with ether. The aqueous layer was acidified with 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure to give the title compound as a yellow amorphous substance (1.96 g, 55%).

Workup

  1. customsynthesized separately
  2. customThe solvent was evaporated under reduced pressure
  3. additionthe residue was diluted with water
  4. washwashed with ether
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-aaaac3f4f39e4bb3a1ce955e5044c64c
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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