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

HRID 83969Notes

Reaction equation

HRID 83969 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) is dissolved into ethyl acetate (60 mL), and 5% Pt/C (9.0 g) is added to the solution. The mixture is stirred under a H2 atmosphere (90 psi) for 24 hours and then filtered. After removal of the ethyl acetate, the residue is purified by chromatography on silica gel eluted with hexane to produce the target compound (29.0 g, 79.9% yield). 1HNMR (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. additionis added to the solution
  2. filtrationfiltered
  3. customAfter removal of the ethyl acetate
  4. customthe residue is purified by chromatography on silica gel
  5. washeluted with hexane

Sources & evidence

ORD record
ord-74217820f7c1481b88baac4af6a791b5
Source dataset
uspto-grants-2014_09
Patent number
US08846855B2

Reaction notes

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