Ethyl Acetate → HCID 59516853, Verbindung

HRID 1161394Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1161394
[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]

Komponenten

7

Edukt 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

Produkt 1

HCID 59516853HCID 59516853, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2733225Ytterbium triflateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2f1d6e3c84004ddf80891020adf12236
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816522B2

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