Reaktion #171150

Reaktionsgleichung

2-bromo-3-decanyldithieno[3,2-b:2′,3′-d]thiophene

1-decyne

→

compound

Ausbeute 93.0%

3-decanyl-6-dec-1-ynyldithieno[3,2-b:2′,3′-d]thiophene

Ausbeute 93.0%

Lösungsmittel

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThis mixture is bubbled with nitrogen for 5 minutes
2. 2
   SonstigeTriethylamine is evaporated
3. 3
   workup.ADDITIONhexane (150 mL) is added
4. 4
   FiltrationThe mixture is filtered
5. 5
   Sonstigeto remove solid salts
6. 6
   Waschenthe organic layer is washed with 1M hydrochloric acid (50 mL) and brine (50 mL)
7. 7
   Trocknendried over MgSO4
8. 8
   SonstigeThe solvent is removed in vacuo
9. 9
   Sonstigethe residue is purified by chromatography on silica gel eluting with hexane

Vorschrift

2-bromo-3-decanyldithieno[3,2-b:2′,3′-d]thiophene (92) (4.16 g, 0.01 mol) is mixed with 1-decyne (3.6 g, 0.026 mol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol) and copper(I) iodide (0.19 g, 1.0 mmol) in triethylamine (80 mL). This mixture is bubbled with nitrogen for 5 minutes and then heated to 130° C. under argon for 16 hours. Triethylamine is evaporated and hexane (150 mL) is added. The mixture is filtered to remove solid salts and the organic layer is washed with 1M hydrochloric acid (50 mL) and brine (50 mL), then dried over MgSO4. The solvent is removed in vacuo, and the residue is purified by chromatography on silica gel eluting with hexane to yield the target compound (3.87 g, 93.0% yield). 1HNMR (CD2Cl2): δ 7.36 (d, 1H), 7.30 (d, 1H), 2.82 (t, 2H), 2.49 (t, 2H), 1.63-1.27 (m, 28H), 0.88 (m, 6H).

Quelle