(Z)-Benzaldehyde oxime → HCID 67099896, compound

HRID 1868703Notes

Reaction equation

HRID 1868703 reaction equation
C(=N[OH:9])C1C=CC=CC=1.[H-].[Na+].[C:12]([C:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]#[C:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])([CH3:20])[C:15]([O:17]CC)=O)#[N:13]>CN(C=O)C.O1CCOCC1>[C:12]([C:14]1([CH3:20])[C:21]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:27]([OH:9])=[C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:15]1=[O:17])#[N:13]

Participants

6

Reactant 3

HCID 12143(Z)-Benzaldehyde oximeHCID 24758Sodium hydrideHCID 67099414HCID 67099414, compound

Product 1

HCID 67099896HCID 67099896, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of benzaldehyde oxime (0.37 mL, 3.7 mmol) in dry DMF (4 mL) was added to a stirred suspension of NaH (0.16 mL, 3.7 mmol) in dry dioxane (50 mL) in a nitrogen atmosphere at room temperature. After 30 minutes, a solution of ethyl 3-(2-(2-cyano-1-ethoxy-1-oxopropan-2-yl)phenyl)propiolate (1.12 g, 3.7 mmol) was added in dry DMF (5 mL), and the solution was stirred overnight. The solvent was removed under vacuum, and water was added to the residue. The product was extracted with EtOAc. The organic layer was washed with water, dried with MgSO4, concentrated in vacuo, and purified by silica flash chromatography eluting with 0-30% EtOAc/hexane. MS (m/z)=272 (M+H)+.

Workup

  1. customThe solvent was removed under vacuum, and water
  2. additionwas added to the residue
  3. extractionThe product was extracted with EtOAc
  4. washThe organic layer was washed with water
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated in vacuo
  7. custompurified by silica flash chromatography
  8. washeluting with 0-30% EtOAc/hexane

Sources & evidence

ORD record
ord-40542f43ca044118ae0d61a17523b188
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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