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

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Reaction Steps

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.

Provenance & Evidence