Trifluoroacetic acid → 3-(2,2-Dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-benzonitrile

HRID 859368

Reaktionsgleichung

Reaktionsgleichung von HRID 859368
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7])#[N:2].C[Si]([C:16]([Si](C)(C)C)(C([O-])=O)[C:17]([O-:19])=[O:18])(C)C.[Li][CH2:28][CH2:29][CH2:30]C.[C:32]([OH:38])([C:34](F)(F)F)=[O:33]>CCOCC.C(OC(C)=C)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([C:6](=[O:7])[CH2:16][C:17]([OH:19])=[O:18])[CH:9]=[CH:10][CH:11]=1)#[N:2].[CH3:30][C:29]1([CH3:28])[O:7][C:6]([C:5]2[CH:4]=[C:3]([CH:11]=[CH:10][CH:9]=2)[C:1]#[N:2])=[CH:34][C:32](=[O:33])[O:38]1

Komponenten

8

Edukt 4

HCID 6422Trifluoroacetic acidHCID 3084833-Cyanobenzoyl chlorideHCID 222245802,2-Bis(trimethylsilyl)propanedioateHCID 178418339Butyllithium

Produkt 2

HCID 117363373-(2,2-Dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-benzonitrileHCID 222245603-(3-Cyano-phenyl)-3-oxo-propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 7916Isopropenyl acetateLösungsmittel

Versuchsvorschrift

The 3-(3-cyano-phenyl)-3-oxo-propionic acid was prepared from 3-cyanobenzoyl chloride (828 mg, 5 mmol) and bis(trimethylsilyl)malonate (2.56 mL, 10 mmol) with n-BuLi (1.6M in hexane, 6.25 mL) in ether at −60° C. to 0° C. according to general procedure H (method c2). The crude material (1.04 g) was transformed into the title compound by stirring in isopropenyl acetate and TFA according to general procedure J (method a). Obtained as a light yellow solid (0.8 g).

Quellen und Nachweise

ORD-Eintrag
ord-6bb19336f5d24d2b93e1d1e4aa7c53af
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07151098B2

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