3,4-(Methylenedioxy)phenylmagnesium bromide solution → 1-(1,3-Benzodioxol-5-yl)-2-[8-(benzyloxy)-5-chloroquinolin-7-yl]ethanol

HRID 551120Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 551120
[CH2:1]([O:8][C:9]1[C:10]([CH2:20][CH:21]=[O:22])=[CH:11][C:12]([Cl:19])=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]1[O:31][C:30]2[C:25](=[CH:26][CH:27]=[C-:28][CH:29]=2)[O:24]1.[Mg+2].[Br-].C1(C)C=CC=CC=1.O1CCCC1>O1CCCC1>[O:24]1[C:25]2[CH:26]=[CH:27][C:28]([CH:21]([OH:22])[CH2:20][C:10]3[C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[C:18]4[C:13]([CH:14]=[CH:15][CH:16]=[N:17]4)=[C:12]([Cl:19])[CH:11]=3)=[CH:29][C:30]=2[O:31][CH2:23]1

Komponenten

5

Edukt 3

HCID 44296443,4-(Methylenedioxy)phenylmagnesium bromide solutionHCID 22635083Tetrahydrofuran tolueneHCID 59829696[8-(Benzyloxy)-5-chloroquinolin-7-yl]acetaldehyde

Produkt 1

HCID 598296621-(1,3-Benzodioxol-5-yl)-2-[8-(benzyloxy)-5-chloroquinolin-7-yl]ethanolAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a stirring solution of [8-(benzyloxy)-5-chloroquinolin-7-yl]acetaldehyde (0.380 mmol) in tetrahydrofuran (4 mL) at −78° C. was dropwise added a 1M solution of 3,4-(methylenedioxy)phenylmagnesium bromide in 1:1 toluene/tetrahydrofuran (0.380 mmol, 1.0 eq.) and stirring at −78° C. was continued for 10 min. The reaction mixture was then allowed to warm to room temperature and was stirred 1 h then quenched with saturated aqueous sodium bicarbonate solution (2 mL). After stirring 15 min the reaction mixture was extracted with ethyl acetate (3×5 mL) and the combined organic layers were dried (MgSO4), filtered and concentrated to give a brown oil that was purified by column chromatography using 30% ethyl acetate/hexanes to give the final product as a white foam (0.126 mmol, 33%). MS (ESI) m/z 434.2; HRMS: calcd for C25H20ClNO4+H+, 434.11536; found (ESI, [M+H]+ Obs'd), 434.1150.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. stirringwas stirred 1 h
  3. customthen quenched with saturated aqueous sodium bicarbonate solution (2 mL)
  4. stirringAfter stirring 15 min the reaction mixture
  5. extractionwas extracted with ethyl acetate (3×5 mL)
  6. dry with materialthe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a brown oil that
  10. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7803691c48ab497695f0c375c6b125d5
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947712B2

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