Ethyl Acetate → 5-(Tert-butyldiphenylsilanyloxy)-3-(4-trifluoromethylphenyl)-pentanenitrile

HRID 406373

Reaktionsgleichung

Reaktionsgleichung von HRID 406373
[Si:1]([O:18][CH2:19][CH2:20][CH:21]([C:26]1[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=1)[CH2:22][C:23]([NH2:25])=O)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N12CCCN=C1CCCCC2.P(Cl)(Cl)(OC)=O.C(OCC)(=O)C>C(Cl)Cl.CCCCCCC>[Si:1]([O:18][CH2:19][CH2:20][CH:21]([C:26]1[CH:27]=[CH:28][C:29]([C:32]([F:33])([F:34])[F:35])=[CH:30][CH:31]=1)[CH2:22][C:23]#[N:25])([C:14]([CH3:15])([CH3:17])[CH3:16])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 69611Methyl dichlorophosphateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 666301385-(Tert-butyldiphenylsilanyloxy)-3-(4-trifluoromethylphenyl)pentanoic acid amide

Produkt 1

HCID 667780115-(Tert-butyldiphenylsilanyloxy)-3-(4-trifluoromethylphenyl)-pentanenitrileAusbeute 97,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8900HeptaneLösungsmittel

Versuchsvorschrift

5-(tert-Butyldiphenylsilanyloxy)-3-(4-trifluoromethylphenyl)pentanoic acid amide (640 mg) was dissolved in methylene chloride (13 mL), and 1,8-diazabicyclo[5,4,0]undec-7-ene (862 μL) and methyl dichlorophosphate (301 μL) were added at 0° C. After stirring at room temperature for 1.5 hours, the reaction was terminated with a saturated sodium bicarbonate aqueous solution. The organic layer was washed with brine and then dried over magnesium sulfate. Concentration under reduced pressure gave an oil. The oil was allowed to pass through a silica gel pad (mobile phase:ethyl acetate:heptane=1:2) to obtain the title compound (600 mg).

Aufarbeitung

  1. customthe reaction was terminated with a saturated sodium bicarbonate aqueous solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationConcentration under reduced pressure
  5. customgave an oil

Quellen und Nachweise

ORD-Eintrag
ord-0c8a6ef0d45e484282c68aa172cda9a4
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754100B2

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