3-(8-(1,3-Dioxolan-2-yl)octyloxy)benzaldehyde → (3-(8-(1,3-Dioxolan-2-yl)octyloxy)phenyl)(thiophen-2-yl)methanol

HRID 332653Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 332653
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[O:19].[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[Mg]Br>C1COCC1>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:18]([C:24]2[S:23][CH:27]=[CH:26][CH:25]=2)[OH:19])[CH:20]=[CH:21][CH:22]=1

Komponenten

4

Edukt 2

HCID 866768973-(8-(1,3-Dioxolan-2-yl)octyloxy)benzaldehydeHCID 178418438HCID 178418438, Verbindung

Produkt 1

HCID 71093201(3-(8-(1,3-Dioxolan-2-yl)octyloxy)phenyl)(thiophen-2-yl)methanolAusbeute 88,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a stirred solution of 3-(8-(1,3-dioxolan-2-yl)octyloxy)benzaldehyde (1.0 g, 3.25 mmol) in THF (30 mL) at −78° C. under an atmosphere of nitrogen, a solution of 2-thienylmagnesium bromide (1M in THF, 4.23 mL, 4.23 mmol) was added over 10 minutes. After stirring at −78° C. for 1 hour, the reaction was allowed to warm to RT and stirred for 16 hours. The reaction was quenched with saturated aqueous ammonium chloride solution and extracted with ethyl acetate (×3). The combined organic extracts were washed with brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with 0-50% ethyl acetate in iso-hexane to afford the title compound (1.12 g, 87%).

Aufarbeitung

  1. temperatureto warm to RT
  2. stirringstirred for 16 hours
  3. customThe reaction was quenched with saturated aqueous ammonium chloride solution
  4. extractionextracted with ethyl acetate (×3)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude material was purified by silica gel chromatography
  10. washeluting with 0-50% ethyl acetate in iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-ed5b0dca12ec40b5b5c3acb9aca160ab
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877774B2

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