Hexane → 2-(1,4,5-Trimethoxy-3-naphthylcarbonyl)-5-(2-methyl-dioxolan-2-yl)-6-oxa-bicyclo[3,2,1]octan-7-one

HRID 2165444Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2165444
[CH3:1][CH2:2][CH2:3]CCC.[CH2:7]([Li])CCC.CO[C:14]([CH:16]1[CH2:22][CH2:21][C:20]2([C:24]3([CH3:29])[O:28][CH2:27][CH2:26][O:25]3)[CH2:23][CH:17]1[C:18](=[O:30])[O:19]2)=[O:15].[CH3:31][O:32][CH:33]1[C:39](=[C:40]=[O:41])[CH2:38][C:37]2(C3(C)OCCO3)[CH2:42][CH:34]1[C:35](=O)[O:36]2>O1CCCC1>[CH3:35][O:36][C:37]1[C:38]2[C:39](=[C:40]([O:41][CH3:7])[CH:1]=[CH:2][CH:3]=2)[C:33]([O:32][CH3:31])=[C:34]([C:14]([CH:16]2[CH2:22][CH2:21][C:20]3([C:24]4([CH3:29])[O:25][CH2:26][CH2:27][O:28]4)[CH2:23][CH:17]2[C:18](=[O:30])[O:19]3)=[O:15])[CH:42]=1

Komponenten

6

Edukt 4

HCID 8058HexaneHCID 134534872-Methoxycarbonyl-5-(2-methyldioxolan-2-yl)-6-oxabicyclo[3,2,1]octan-7-oneHCID 867440952-Methoxy-carbonyl-5-(2-methyl-dioxolan-2-yl)-6-oxa-bicyclo[3,2,1]-octan-7-oneHCID 178418339Butyllithium

Produkt 1

HCID 134534882-(1,4,5-Trimethoxy-3-naphthylcarbonyl)-5-(2-methyl-dioxolan-2-yl)-6-oxa-bicyclo[3,2,1]octan-7-oneAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

7 ml of a 1.65 M hexane solution of n-butyllithium was dissolved in 30 ml of anhydrous tetrahydrofuran. To the solution was added at -78° C a solution of 3.3 g of 1,4,5-trimethoxy-3-bromo-naphthalene (VI, R=OCH3) in 30 ml of anhydrous tetrahydrofuran. 2,5 g of 2-methoxy-carbonyl-5-(2-methyl-dioxolan-2-yl)-6-oxa -bicyclo[3,2,1]-octan-7-one, prepared as described in Example 3, was dissolved in 50 ml of anhydrous tetrahydrofuran and added to the reaction mixture. The reaction mixture was stood for 1 hour at -78° C and then quenched with acetic acid. The solvent was removed in vacuo. The residue was purified by silica gel column chromatograhy, giving 3 g (73% yield) of the title compound. m/z 456 (M+.).

Aufarbeitung

  1. additionadded to the reaction mixture
  2. customquenched with acetic acid
  3. customThe solvent was removed in vacuo
  4. customThe residue was purified by silica gel column chromatograhy

Quellen und Nachweise

ORD-Eintrag
ord-5b14eb8ac7c3405285f0dddb77d8773f
Quelldatensatz
uspto-grants-1990_07
Patentnummer
US04939282

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