2-Dec-1-ynyl-3-decanyldithieno[2,3-d:2',3'-d']thieno [3,2-b:4,5-b']dithiophene → 2,3-Didecanyldithieno[2,3-d:2',3'-d']thieno[3,2-b:4,5-b']dithiophene

HRID 1175104Notes

Reaction equation

HRID 1175104 reaction equation
[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]

Participants

4

Reactant 1

HCID 669248432-Dec-1-ynyl-3-decanyldithieno[2,3-d:2',3'-d']thieno [3,2-b:4,5-b']dithiophene

Product 1

HCID 669253352,3-Didecanyldithieno[2,3-d:2',3'-d']thieno[3,2-b:4,5-b']dithiophene

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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. 1H NMR: 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). 13C NMR: 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.

Workup

  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
  5. customto produce the target compound (2.00, 90.5%)

Sources & evidence

ORD record
ord-ef6b38b981b64a10978e9d4633594afd
Source dataset
uspto-grants-2010_11
Patent number
US07838623B2

Reaction notes

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