Water → HCID 58238644, Verbindung

HRID 41328

Reaktionsgleichung

Br[C:2]1[C:3]2[C:8]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[CH:15]=1)=[CH:7][CH:6]=[CH:5][CH:4]=2.[Li]C(C)(C)C.[CH3:21][O:22][C:23]1[CH:36]=[CH:35][CH:34]=[CH:33][C:24]=1/[N:25]=[CH:26]/[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>C1COCC1.CCCCC>[CH3:21][O:22][C:23]1[CH:36]=[CH:35][CH:34]=[CH:33][C:24]=1[NH:25][CH:26]([C:2]1[C:3]2[C:8]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[CH:15]=1)=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Komponenten

Reaktionsbedingungen

Temperatur: -80 °C

Versuchsvorschrift

To a solution of 5.14 g (20.0 mmol) of 9-bromophenanthrene in 80 mL of THF, 26.7 mL (40.1 mmol) of 1.5 M tBuLi in pentane was added with vigorous stirring at −80° C. This mixture was additionally stirred for 1 hr at this temperature and then slowly warmed to room temperature. The resulting mixture was stirred for 30 min at ambient temperature and then cooled to −80° C. A solution of 4.22 g (20.0 mol) of 9 in 50 mL of THF was added. To the resulting mixture, 5 mL of water was added, and then this mixture was evaporated to dryness. The title product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-diethyl ether=40:1, vol.). Yield 7.32 g (94%).

Aufarbeitung

stirringThis mixture was additionally stirred for 1 hr at this temperature
temperatureslowly warmed to room temperature
stirringThe resulting mixture was stirred for 30 min at ambient temperature
temperaturecooled to −80° C
customthis mixture was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag: ord-fcd8a70a31eb43d696813268c1095200
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08530593B2

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