9-Heptadecanone → 9-([2,2'-Bithiophen]-3-yl)heptadecan-9-ol

HRID 2193819

Reaktionsgleichung

Reaktionsgleichung von HRID 2193819
Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[S:8][CH:9]=[CH:10][CH:11]=1.C([Li])CCC.[CH3:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25](=[O:34])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>C(OCC)C>[S:4]1[CH:5]=[CH:6][C:2]([C:25]([OH:34])([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17])=[C:3]1[C:7]1[S:8][CH:9]=[CH:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 108879-HeptadecanoneHCID 36136783-Bromo-2,2'-bithiopheneHCID 178418339Butyllithium

Produkt 1

HCID 585680009-([2,2'-Bithiophen]-3-yl)heptadecan-9-olAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

3-Bromo-2,2′-bithiophene (IIIa) (5.00 g, 20 mmol) in dry diethylether (170 mL) was added slowly to a solution of n-butyllithium (1.6 M in hexane, 12.5 mL, 20 mmol) in dry diethylether (170 mL) at −78° C. over 2 h under N2. The mixture was stirred for 15 minutes at the same temperature. Heptadecan-9-one (6.22 g, 24 mmol) was added to the mixture at −78° C., followed by stirring overnight at room temperature. The reaction was quenched with an aqueous NH4Cl-solution (2.5 M, 85 mL) and water (85 mL) at 0° C. The organic phase was separated and the aqueous phase was extracted with diethylether. The combined organic phases were washed with brine, dried over MgSO4 and evaporated under reduced pressure to give a crude oil. The oily residue was purified by gradient column chromatography (eluent hexane/EtOAc 95:5) to afford the title compound (IIe) as a yellow oil (6.3 g, 75%). 1H-NMR (CDCl3): δ=7.34 (dd, J=5.1 Hz, J=1.3 Hz, 1H), 7.22 (d, J=5.3 Hz, 1H), 7.07 (dd, J=3.5 Hz, J=1.2 Hz, 1H), 6.99 (dd, J=5.1, J=3.5 Hz, 1H), 6.97 (d, J=5.3 Hz, 1H), 2.36 (t, J=7.7 Hz, 4H), 1.39-1.07 (m, 20H), 0.91-0.81 (m, 6H).

Aufarbeitung

  1. stirringby stirring overnight at room temperature
  2. customThe reaction was quenched with an aqueous NH4Cl-solution (2.5 M, 85 mL) and water (85 mL) at 0° C
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted with diethylether
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated under reduced pressure
  8. customto give a crude oil
  9. customThe oily residue was purified by gradient column chromatography (eluent hexane/EtOAc 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-4a84c1ad46d2421b907c6689df79cd50
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329923B2

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