Reaktionsgleichung
C([N-]C(C)C)(C)C.[Li+].[CH3:9]N1CCCN(C)C1=O.[Cl:18][C:19]1[C:20]([CH3:27])=[C:21]([CH:24]=[CH:25][CH:26]=1)[C:22]#[N:23].[C:28](=[O:30])=[O:29].[OH-].[Na+]>O.O1CCCC1>[CH3:9][CH:27]([C:20]1[C:21]([C:22]#[N:23])=[CH:24][CH:25]=[CH:26][C:19]=1[Cl:18])[C:28]([OH:30])=[O:29]Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
Add a 2M solution of lithium diisopropylamide in tetrahydrofuran (62.6 mL, 461.8 mmol) to tetrahydrofuran (1 L) at −78° C. Slowly add 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (19.94 mL, 164.91 mmol) followed by drop-wise addition of 3-chloro-2-methyl-benzonitrile (20 g, 131.93 mmol). Maintain the mixture at −78° C. with stirring for 5 min. Purge the reaction vessel with carbon dioxide (1 L; 25.65 moles) for 15 min. Add water (100 mL) and stir for 2 hr. Add 10M aqueous solution of sodium hydroxide to increase the pH of the aqueous phase to >12. Separate the aqueous layer and wash with diethyl ether. Acidify the aqueous layer with concentrated hydrochloric acid to pH-1 and extract with ethyl acetate. Separate the organic phase and dry over sodium sulfate. Filter and concentrate to dryness to yield the title compound as an off white solid (16.0 g; 81.80 mmol). MS (m/z): 195.9 (M+1).
Aufarbeitung
- temperatureto increase the pH of the aqueous phase to >12
- customSeparate the aqueous layer
- washwash with diethyl ether
- extractionextract with ethyl acetate
- customSeparate the organic phase
- dry with materialdry over sodium sulfate
- filtrationFilter
- concentrationconcentrate to dryness
Quellen und Nachweise
- ORD-Eintrag
- ord-b07bdaf260d248c89b26f14d1a820c65
- Quelldatensatz
- uspto-grants-2015_02
- Patentnummer
- US08962654B2
Verknüpfte Notizen
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