Sulfuric Acid → 4,4-Diethyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene

HRID 2193810Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2193810
OS(O)(=O)=O.[S:6]1[CH:10]=[CH:9][C:8]([C:11](O)([CH2:14][CH3:15])[CH2:12][CH3:13])=[C:7]1[C:17]1[S:18][CH:19]=[CH:20][CH:21]=1.C(Cl)Cl>O>[CH2:12]([C:11]1([CH2:14][CH3:15])[C:21]2[CH:20]=[CH:19][S:18][C:17]=2[C:7]2[S:6][CH:10]=[CH:9][C:8]1=2)[CH3:13]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 498402833-(2,2'-Bithiophene-3-yl)pentan-3-ol

Produkt 1

HCID 498402844,4-Diethyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

H2SO4 (7.0 mL) was added dropwise to 3-(2,2′-bithiophene-3-yl)pentan-3-ol (IIa) (2.67 g, 11 mmol) under stirring at room temperature. After stirring for 12 h, CH2Cl2 (100 mL) and water (100 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 pure dark yellow oil (Ia) (1.2 g, 47%). 1H-NMR (CDCl3): δ=7.21 (d, J=4.8 Hz, 2H), 7.00 (d, J=4.8 Hz, 2H), 1.98 (q, J=6.8 Hz), 4H), 0.70 (t, J=7.0 Hz, 6H). 13C-NMR (CDCl3): δ=157.89, 137.36, 125.09, 122.16, 54.76, 30.71, 9.74.

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 pure dark yellow oil (Ia) (1.2 g, 47%)

Quellen und Nachweise

ORD-Eintrag
ord-3a3dcd1179d2423093038e3fad87901f
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329923B2

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