Sulfuric Acid → 4-Nonyl-4-methyl-4H-cyclopenta[1,2-b:5,4-b']dithiophene

HRID 2193814Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2193814
OS(O)(=O)=O.[S:6]1[CH:10]=[CH:9][C:8]([C:11](O)([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH3:12])=[C:7]1[C:23]1[S:24][CH:25]=[CH:26][CH:27]=1.C(Cl)Cl>O>[CH2:13]([C:11]1([CH3:12])[C:27]2[CH:26]=[CH:25][S:24][C:23]=2[C:7]2[S:6][CH:10]=[CH:9][C:8]1=2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 585681592-(2,2'-Bithiophene-3-yl)undecan-2-ol

Produkt 1

HCID 498402854-Nonyl-4-methyl-4H-cyclopenta[1,2-b:5,4-b']dithiophene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

H2SO4 (1.33 mL) was added dropwise to 2-(2,2′-bithiophene-3-yl)undecan-2-ol (IIc) (0.70 g, 2.08 mmol) under stirring at room temperature. After stirring for 12 h, CH2Cl2 (15 mL) and water (15 mL) were added. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined organic extracts were successively washed with saturated NaHCO3 and brine. After drying over MgSO4, the solvent was removed in vacuo. The crude oil was purified with column chromatography (eluent hexane) to afford a pure dark yellow oil (Ic) (0.106 g, 16.0%). 1H-NMR (CDCl3): δ=7.13 (d, J=4.8 Hz, 2H), 6.94 (d, J=4.9 Hz, 2H), 1.82-1.75 (m, 2H), 1.41 (s, 3H), 1.29-1.07 (m, 14H), 0.84 (t, J=6.6 Hz, 3H). 13C-NMR (CDCl3): δ=160.04, 136.50, 125.27, 121.95, 49.53, 39.66, 32.50, 30.63, 30.36, 30.20, 30.07, 29.91, 25.65, 24.36, 23.32, 14.77.

Aufarbeitung

  1. stirringAfter stirring for 12 h
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. washThe combined organic extracts were successively washed with saturated NaHCO3 and brine
  5. dry with materialAfter drying over MgSO4
  6. customthe solvent was removed in vacuo
  7. customThe crude oil was purified with column chromatography (eluent hexane)
  8. customto afford a pure dark yellow oil (Ic) (0.106 g, 16.0%)

Quellen und Nachweise

ORD-Eintrag
ord-aa430f8afbbc43b5ba64b26c82a86d00
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329923B2

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