Tri-o-tolylphosphine → Methyl 2-acetylamino-3-(4-benzyloxy-3,5-dimethyl-phenyl)-acrylate

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Reaktionsgleichung

[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12](Br)=[CH:11][C:10]=1[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]([NH:21][C:22](=[CH2:27])[C:23]([O:25][CH3:26])=[O:24])(=[O:20])[CH3:19].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(N(CC)CC)C.C(#N)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:18]([NH:21][C:22](=[CH:27][C:12]1[CH:13]=[C:14]([CH3:15])[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([CH3:17])[CH:11]=1)[C:23]([O:25][CH3:26])=[O:24])(=[O:20])[CH3:19]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

Under a nitrogen atmosphere a mixture of 40.0 g (137 mmol) 2-benzyloxy-5-bromo-1,3-dimethylbenzene and 24.1 g (165 mmol) methyl 2-acetylamino-acrylate in 420 mL triethylamine and 200 mL acetonitrile was combined with 3.5 g (11.2 mmol) tri-o-tolyl-phosphane and 2.5 g (11.1 mmol) Pd(OAc)2 and stirred for 18 h at 80° C. The precipitate was suction filtered, the filtrate was evaporated down i.vac. and combined with 800 mL DCM and 800 mL water. The organic phase was separated off, suction filtered through Na2SO4, the solvent was eliminated i.vac., the residue was stirred with EtOAc, suction filtered and dried i.vac.

Aufarbeitung

filtrationfiltered
customthe filtrate was evaporated down i.vac
customThe organic phase was separated off
filtrationsuction filtered through Na2SO4
stirring, the residue was stirred with EtOAc, suction
filtrationfiltered
customdried i.vac

Quellen und Nachweise

ORD-Eintrag: ord-6d35d503ee0f4e7da2b75a700a59081d
Quelldatensatz: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07696209B2

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