Diethyl Ether → HCID 86612522, compound

HRID 2219788Notes

Reaction equation

HRID 2219788 reaction equation
[CH3:1][C:2](=[N:4][OH:5])[CH3:3].CC(C)([O-])C.[Na+].[C:12]([O:16][C:17](=[O:41])[N:18]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[C:34](F)[CH:33]=2)=[CH:27][CH:26]=1)[CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])([CH3:15])([CH3:14])[CH3:13].CCOCC>CN(C=O)C>[C:12]([O:16][C:17](=[O:41])[N:18]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[C:34]([O:5][N:4]=[C:2]([CH3:3])[CH3:1])[CH:33]=2)=[CH:27][CH:26]=1)[CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])([CH3:14])([CH3:15])[CH3:13]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 67180Acetone, oximeHCID 23676156Sodium t-butoxideHCID 68173253HCID 68173253, compound

Product 1

HCID 86612522HCID 86612522, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of acetone oxime (1.1 equiv) in DMF was added sodium tert-butoxide (1.1 equiv). The mixture was stirred at room temperature for 45 min followed by the addition of a solution of compound from Step 3 (1 equiv). The reaction was stirred at room temperature for 3 hours. It was poured on NH4Cl sat and ether. Washed with water and dry over magnesium sulphate, filtered and concentrate. It was purified by silica gel chromatography using hexane:ethyl acetate (15%) to afford the title compound as a white solid.

Workup

  1. stirringThe reaction was stirred at room temperature for 3 hours
  2. additionIt was poured on NH4Cl
  3. washWashed with water
  4. dry with materialdry over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrate
  7. customIt was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0f3d7e422dc3498d8af4303e6161f549
Source dataset
uspto-grants-2008_08
Patent number
US07414132B2

Reaction notes

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