Trimethyltin chloride → 2-(Benzo[d]oxazol-2-yl)benzaldehyde

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Reaktionsgleichung

C([Sn](CCCC)(CCCC)[C:6]1[O:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[N:10]=1)CCC.C([Sn](Cl)(CCCC)CCCC)CCC.C[Sn](Cl)(C)C.Br[C:43]1[CH:50]=[CH:49][CH:48]=[CH:47][C:44]=1[CH:45]=[O:46]>C1(C)C(C)=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[O:7]1[C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[N:10]=[C:6]1[C:43]1[CH:50]=[CH:49][CH:48]=[CH:47][C:44]=1[CH:45]=[O:46]

Komponenten

Reaktionsbedingungen

Temperatur: 115 °C

Versuchsvorschrift

A mixture of 12.5 g of 2-tributylstannylbenzoxazole (prepared by the method of P. Jutzi and W. Gilge, J. Organometallic Chem. 1983, 246, 159, using tributyltin chloride as a less toxic replacement for trimethyltin chloride) 5.66 g 2-bromobenzaldehyde, and 0.46 g tetrakis(triphenylphosphine)-palladium (0) in 300 ml of anhydrous xylene under a nitrogen atmosphere was heated to 115° C. for 12 h. The reaction mixture was cooled to room temperature and evaporated to dryness under reduced pressure. The resulting oil was purified by chromatography on silica eluting with ethyl acetate-heptane (1:5) to afford 5.8 g of 2-(benzoxazol-2-yl)benzaldehyde, GC-M.S. (E.I.) (M/Z): 223 [M+ ].

Aufarbeitung

customprepared by the method of P
temperatureThe reaction mixture was cooled to room temperature
customevaporated to dryness under reduced pressure
customThe resulting oil was purified by chromatography on silica eluting with ethyl acetate-heptane (1:5)

Quellen und Nachweise

ORD-Eintrag: ord-983363f6fcd943e9aa17f0ace0e5a2f2
Quelldatensatz: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06080773

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