3-Decanyl-6-dec-1-ynyldithieno[3,2-b:2',3'-d]thiophene → 2,3-Didecanyldithieno[3,2-b:2',3'-d]thiophene

HRID 646548Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 646548
C([C:11]1[C:18]2[S:17][C:16]3[CH:19]=[C:20]([C:22]#[C:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[S:21][C:15]=3[C:14]=2[S:13][CH:12]=1)CCCCCCCCC>[Pt].C(OCC)(=O)C>[CH2:22]([C:20]1[S:21][C:15]2[C:14]3[S:13][CH:12]=[CH:11][C:18]=3[S:17][C:16]=2[C:19]=1[CH2:11][CH2:18][CH2:14][CH2:15][CH2:16][CH2:19][CH2:20][CH2:22][CH2:23][CH3:24])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Komponenten

4

Edukt 1

HCID 669250153-Decanyl-6-dec-1-ynyldithieno[3,2-b:2',3'-d]thiophene

Produkt 1

HCID 161034772,3-Didecanyldithieno[3,2-b:2',3'-d]thiopheneAusbeute 160 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23939PlatinumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3-decanyl-6-dec-1-ynyldithieno[3,2-b:2′,3′-d]thiophene (93) (36.0 g, 0.076 mol) was dissolved into ethyl acetate (60 mL). To this solution, 5% Pt/C (9.0 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 (29.0 g, 79.9%). 1HNMR: solvent, CD2Cl2 δ 7.29 (d, 1H), 7.27 (d, 1H), 2.80 (t, 2H), 2.67 (t, 2H), 1.68-1.27 (m, 32H), 0.88 (m, 6H). 13CNMR. 142.88, 140.75, 139.82, 131.69, 131.37, 126.69, 125.04, 120.94, 32.16, 29.85 (m,overlap), 22.93, 14.11.

Aufarbeitung

  1. filtrationThe solution was then filtered
  2. customAfter removal of the ethyl acetate
  3. customthe residue was purified by chromatography on silica gel
  4. washeluted with hexane

Quellen und Nachweise

ORD-Eintrag
ord-80847fbaeb454627887f0ac36ca3fccd
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07705108B2

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