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

HRID 1803011Notes

Reaction equation

HRID 1803011 reaction equation
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]

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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.

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

Sources & evidence

ORD record
ord-42ebcfba550942169090f3340fb7e8f4
Source dataset
uspto-grants-2013_01
Patent number
US08349998B2

Reaction notes

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