Ethyl Acetate → HCID 59516853, compound

HRID 2079123Notes

Reaction equation

HRID 2079123 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[N:3]=1.C[Si]([C:18]#[N:19])(C)C.[Si:20]([O:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][C:29]=1[O:36][CH3:37])([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21].C(OCC)(=O)C>ClCCl.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3]>[Si:20]([O:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]([NH:13][C:10]2[CH:11]=[CH:12][C:7]([C:4]3[N:3]=[C:2]([CH3:1])[O:6][N:5]=3)=[CH:8][CH:9]=2)[C:18]#[N:19])=[CH:30][C:29]=1[O:36][CH3:37])([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 82115Trimethylsilyl cyanideHCID 10539726Benzaldehyde, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methoxy-HCID 181881764-(5-Methyl-1,2,4-oxadiazol-3-yl)aniline

Product 1

HCID 59516853HCID 59516853, compound

Reagents, catalysts & solvents 2

HCID 2733225Ytterbium triflateCatalystHCID 6344DichloromethaneSolvent

Procedure

After adding 3.12 g of 4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine, 3.3 g of MS3A, 1.11 g of Yb(OTf)3 and 4.75 ml of trimethylsilyl cyanide to a solution of 5.0 g of 4-t-butyldimethylsilanyloxy-3-methoxybenzaldehyde [CAS No. 69404-94-0] in 98 ml of dichloromethane under a nitrogen atmosphere, the mixture was stirred at room temperature for 23 hours. Next, 500 ml of ethyl acetate was added to the reaction mixture, the reaction mixture was filtered through celite, and the celite was washed with ethyl acetate. The organic layers were combined and washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The desiccating agent was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (8.45 g) as a crude product.

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. washthe celite was washed with ethyl acetate
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe desiccating agent was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-30ad09dedd5f40c089eb24f33764142b
Source dataset
uspto-grants-2011_04
Patent number
US07928228B2

Reaction notes

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