Formic Acid → 4-(4-Cyanophenyl)-2-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)butanoic acid
Reaktionsgleichung
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([CH2:24][C:25]2[CH:30]=[C:29]([F:31])[C:28]([O:32][Si:33]([CH:40]([CH3:42])[CH3:41])([CH:37]([CH3:39])[CH3:38])[CH:34]([CH3:36])[CH3:35])=[C:27]([F:43])[CH:26]=2)(C(OCC=C)=O)[C:12]([O:14]CC=C)=[O:13])=[CH:5][CH:4]=1)#[N:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.C(O)=O>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11]([CH2:24][C:25]2[CH:26]=[C:27]([F:43])[C:28]([O:32][Si:33]([CH:34]([CH3:36])[CH3:35])([CH:37]([CH3:39])[CH3:38])[CH:40]([CH3:41])[CH3:42])=[C:29]([F:31])[CH:30]=2)[C:12]([OH:14])=[O:13])=[CH:5][CH:4]=1)#[N:2]Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
4720 mg (7.72 mmol) of diallyl 2-[2-(4-cyanophenyl)ethyl]-2-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)malonate, 34.6 mg (0.15 mmol) of palladium(II) acetate and 141.6 mg (0.54 mmol) of triphenylphosphine are stirred in 180 ml of dioxane under argon. Then a solution of 2576 mg (25.60 mmol) of triethylamine and 887.7 mg (19.29 mmol) of formic acid in 90 ml of dioxane is added dropwise, and the mixture is heated at 100° C. for 2 h. The cooled mixture is concentrated and the crude product is chromatographed on silica gel (mobile phase: cyclohexane/ethyl acetate 9:1→2:1→1:1). 3682 mg (97.9% of theory) of the title compound are obtained
Aufarbeitung
- concentrationThe cooled mixture is concentrated
- customthe crude product is chromatographed on silica gel (mobile phase: cyclohexane/ethyl acetate 9:1→2:1→1:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-0ffa7ddc00b54485ae19303172bb6b80
- Quelldatensatz
- uspto-grants-2012_05
- Patentnummer
- US08173704B2
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