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

HRID 5350
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 5350
[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]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8000Boron trifluoride etherateHCID 31214Ethyl orthoformateHCID 81531DiisopropylethylamineHCID 2233794-Bromo-7-methoxy-1-indanone

Produkt 1

HCID 104501054-Bromo-7-methoxy-1-oxo-2,3-dihydro-1H-indene-2-carboxaldehyde diethy acetal

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

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

  1. temperaturecooled to -78° C
  2. temperatureThe reaction was then warmed to -15° C. for 2 h
  3. customquenched in 5% NaHCO3 solution
  4. extractionextracted with methylene chloride
  5. washThe organic extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed
  8. customThe crude product was triturated with cold hexane
  9. 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

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