Reaktionsgleichung
[C:1]([C:11]1[S:27][C:14]2[C:15]3[S:23][C:22]4[C:21]5[S:24][CH:25]=[CH:26][C:20]=5[S:19][C:18]=4[C:16]=3[S:17][C:13]=2[C:12]=1[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]>[Pt].C(OCC)(=O)C>[CH2:1]([C:11]1[S:27][C:14]2[C:15]3[S:23][C:22]4[C:21]5[S:24][CH:25]=[CH:26][C:20]=5[S:19][C:18]=4[C:16]=3[S:17][C:13]=2[C:12]=1[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]Komponenten
Versuchsvorschrift
2-dec-1-ynyl-3-decanyldithieno[2,3-d:2′,3′-d′]thieno[3,2-b:4,5-b′]dithiophene (107) (2.2 g, 4.15 mmol) was dissolved into ethyl acetate (30 mL). To this solution, 5% Pt/C (0.5 g) was added. The mixture was stirred under a H2 atmosphere (90 psi) for 24 hours. The solution was then filtered. After removal of the ethyl acetate, the residue was purified by chromatography on silica gel eluted with hexane to produce the target compound (2.00, 90.5%). Mp. 50.9-52.5° C. 1HNMR: solvent, CD2Cl2 δ 7.41 (d, 1H), 7.33 (d, 1H), 2.83 (t, 2H), 2.50 (t, 2H), 1.73-1.26 (m, 32H), 0.87 (m, 6H). 13CNMR: 140.85, 140.40, 139.93, 133.38, 133.14, 132.22, 129.69, 121.17, 120.09, 98.92, 32.29, 32.25, 29.99, 29.94, 29.72, 29.63, 29.52, 29.33, 29.18, 29.06, 28.94, 23.05, 14.23.
Aufarbeitung
- filtrationThe solution was then filtered
- customAfter removal of the ethyl acetate
- customthe residue was purified by chromatography on silica gel
- washeluted with hexane
- customto produce the target compound (2.00, 90.5%)
Quellen und Nachweise
- ORD-Eintrag
- ord-353785395c00485d92654257119d3c1b
- Quelldatensatz
- uspto-grants-2010_04
- Patentnummer
- US07705108B2
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