(Z)-Benzaldehyde oxime → HCID 67099912, compound

HRID 1868850Notes

Reaction equation

HRID 1868850 reaction equation
C(=N[OH:9])C1C=CC=CC=1.[H-].[Na+].[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([C:26]([C:33]#[N:34])([CH3:32])[C:27]([O:29]CC)=O)=[C:17]([C:19]#[C:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:18]=1>CN(C=O)C.O1CCOCC1>[Cl:12][C:13]1[CH:18]=[C:17]2[C:16](=[CH:15][CH:14]=1)[C:26]([C:33]#[N:34])([CH3:32])[C:27](=[O:29])[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:19]2[OH:9]

Participants

6

Reactant 3

HCID 12143(Z)-Benzaldehyde oximeHCID 24758Sodium hydrideHCID 67099495HCID 67099495, compound

Product 1

HCID 67099912HCID 67099912, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of benzaldehyde oxime (0.16 g, 1.3 mmol) in DMF (3 mL) was added dropwise to a stirred suspension of 60% NaH (0.033 mL, 1.3 mmol) in dry 1,4-dioxane (5 mL) under a nitrogen atmosphere at room temperature. After 30 minutes, a solution of ethyl 3-(5-chloro-2-(2-cyano-1-ethoxy-1-oxopropan-2-yl)phenyl)propiolate (0.445 g, 1.3 mmol) in DMF (3 mL) was added dropwise. The reaction was monitored by LC-MS and, when complete, the solvent was removed. The residual brown oil was dissolved in DCM (50 mL), water (30 mL), and AcOH (2 mL). The layers were separated, and the aqueous layer was extracted with DCM (3×30 mL). The combined organic layers were dried with MgSO4 and concentrated in vacuo. The crude residue was purified using silica flash chromatography with a gradient of 10-50% EtOAc/hexanes. MS m/e=306 (M+H)+.

Workup

  1. customthe solvent was removed
  2. dissolutionThe residual brown oil was dissolved in DCM (50 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with DCM (3×30 mL)
  5. dry with materialThe combined organic layers were dried with MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified

Sources & evidence

ORD record
ord-6c9642950c5549eea279723635b88282
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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