2,8-bis((tert-butyldimethylsilyl)oxy)chromeno[4,3-c]chromen-5(11H)-one → 2-[4-{-1-[4-(2-azepan-1-yl-ethoxy)-phenyl]-1-hydroxy-ethyl}-7-(tert-butyl-dimehyl-silyloxy)-2H-chromen-3-yl]-5-(tert-butyl-dimethyl-silyloxy)-phenol

HRID 2214297Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2214297
Br[C:2]1[CH:17]=[CH:16][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[CH2:18]([Li])CCC.[C:23]([Si:27]([CH3:57])([CH3:56])[O:28][C:29]1[CH:30]=[CH:31][C:32]2[C:33]3[C:46](=[O:47])[O:45][C:44]4[CH:43]=[C:42]([O:48][Si:49]([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:51])[CH3:50])[CH:41]=[CH:40][C:39]=4[C:34]=3[CH2:35][O:36][C:37]=2[CH:38]=1)([CH3:26])([CH3:25])[CH3:24].C[Mg]Br>C1COCC1>[N:9]1([CH2:8][CH2:7][O:6][C:5]2[CH:16]=[CH:17][C:2]([C:46]([C:33]3[C:32]4[C:37](=[CH:38][C:29]([O:28][Si:27]([C:23]([CH3:25])([CH3:24])[CH3:26])([CH3:56])[CH3:57])=[CH:30][CH:31]=4)[O:36][CH2:35][C:34]=3[C:39]3[CH:40]=[CH:41][C:42]([O:48][Si:49]([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:51])[CH3:50])=[CH:43][C:44]=3[OH:45])([OH:47])[CH3:18])=[CH:3][CH:4]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Komponenten

6

Edukt 4

HCID 115915722,8-bis((tert-butyldimethylsilyl)oxy)chromeno[4,3-c]chromen-5(11H)-oneHCID 130635441-[2-(4-Bromophenoxy)ethyl]azepaneHCID 178418339ButyllithiumHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 693277712-[4-{-1-[4-(2-azepan-1-yl-ethoxy)-phenyl]-1-hydroxy-ethyl}-7-(tert-butyl-dimehyl-silyloxy)-2H-chromen-3-yl]-5-(tert-butyl-dimethyl-silyloxy)-phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 1-[2-(4-bromophenoxy)ethyl]-azepane (356 mg, 1.19 mmol) in THF (7.5 mL) at −78° C., was added n-butyl lithium (2.5 M in hexane, 466 μL, 1.17 mmol). The reaction mixture was stirred at −78° C. for 0.5 hours. To the mixture was then added 2,8-bis-(tert-butyl-dimethyl-silyloxy)-11H-chromeno[4,3-c]chromen-5-one, prepared as in Example 22, (149 mg, 0.29 mmol) in THF (3 mL) and the reaction mixture stirred at −78° C. for 1.5 hours. To the mixture was then methyl magnesium bromide (3 M in diethyl ether, 1 mL, 3 mmol) at −78° C. and then stirred at room temperature overnight. The reaction was quenched with aqueous NH4Cl and extracted with ethyl acetate. The organic layer was washed with brine and dried over MgSO4. The remaining solvent was evaporated to yield the crude title product as a yellow oil, which was carried on to the next step without further purification.

Aufarbeitung

  1. stirringthe reaction mixture stirred at −78° C. for 1.5 hours
  2. customThe reaction was quenched with aqueous NH4Cl
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customThe remaining solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-c90e032c6e8840b0a4a40220f79f7ad5
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07105679B2

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