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

HRID 1942864Notes

Reaction equation

HRID 1942864 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-c6936ff645df4c25a0db0ba0228dbc54
Source dataset
uspto-grants-2013_03
Patent number
US08389669B2

Reaction notes

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