Boron trifluoride etherate → 4-Bromo-7-methoxy-1-oxo-2,3-dihydro-1H-indene-2-carboxaldehyde diethy acetal

HRID 5350

Reaktionsgleichung

[CH:1]([O:8][CH2:9][CH3:10])([O:5][CH2:6][CH3:7])OCC.B(F)(F)F.CCOCC.[Br:20][C:21]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]2[C:22]=1[CH2:23][CH2:24][C:25]2=[O:32].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH2:9]([O:8][CH:1]([O:5][CH2:6][CH3:7])[CH:24]1[CH2:23][C:22]2[C:26](=[C:27]([O:30][CH3:31])[CH:28]=[CH:29][C:21]=2[Br:20])[C:25]1=[O:32])[CH3:10]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Triethyl orthoformate (16.5 ml) was cooled to -30° C. and 15.0 ml BF3.Et2O in 50 ml methylene chloride was added. The reaction was warmed to 0° C. for 15 min, and then cooled to -78° C. To the reaction was added 12.05 g of the product from Example 34 in 50 ml methylene chloride, followed by dropwise addition of 19.4 ml diisopropyl ethyl amine. The reaction was then warmed to -15° C. for 2 h, then quenched in 5% NaHCO3 solution and extracted with methylene chloride. The organic extracts were washed with brine, dried (MgSO4), and the solvent removed. The crude product was triturated with cold hexane, and the crystalline product collected to yield 14.60 g of a white solid, mp: 76°-8° C. NMR (CDCl3) δ 1.05 (t, 3H), 1.27 (t, 3H), 3.03 (m, 2 H), 3.30 (m, 1H), 3.43-3.80 (m, 4H), 3.95 (s, 3H), 5.00 (d, 1H), 6.71 (d, 1H), 7.63 (d, 1H).

Aufarbeitung

temperaturecooled to -78° C
temperatureThe reaction was then warmed to -15° C. for 2 h
customquenched in 5% NaHCO3 solution
extractionextracted with methylene chloride
washThe organic extracts were washed with brine
dry with materialdried (MgSO4)
customthe solvent removed
customThe crude product was triturated with cold hexane
customthe crystalline product collected

Quellen und Nachweise

ORD-Eintrag: ord-0c78cd059b394bef950f6b265b6865dc
Quelldatensatz: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05244888

Verknüpfte Notizen

Wird geladen…