Toluene → HCID 69902352, compound

Participants

Reaction Steps

Preparation of 3-[2-benzyloxy-4-(3-chloropropoxy)-5-ethylphenyl]thiophene. A mixture of 4-(benzyloxy)-5-bromo-2-(3-chloropropoxy)ethylbenzene (1.90 g, 5.30 mmol), 3-thiopheneboronic acid (2.00 g, 15.9 mmol), tetrakis(triphenylphosphine)palladium(0) (312 mg, 0.270 mmol), 2 M aqueous sodium carbonate solution (4 mL), and n-propanol (4 mL) in toluene (16 mL) was refluxed for 4 h. The mixture was cooled to room temperature, diluted with diethyl ether, washed once with water and once with saturated sodium chloride solution. The organic layer was dried (magnesium sulfate), filtered, and concentrated in vacuo. Chromatography (silica gel, 5% ethyl acetate/95% hexane) of the residue provided 1.54 g (80%) of the title product as a white solid: mp 65-67° C. 1H NMR (CDCl3) δ 7.58 (d, J=2.8 Hz, 1H), 7.49 (d, J=5.2 Hz, 1H), 7.45-7.30 (m, 7H), 6.62 (s, 1H), 5.13 (s, 2H), 4.14 (t, J=5.8 Hz, 2H), 3.81 (t, J=6.3 Hz, 2H), 2.66 (q, J=7.5 Hz, 2H), 2.29 (quintet, J=6.0 Hz, 2H), 1.24 (t, J=7.5 Hz, 3H); MS FD m/e 386 (p); IR (CHCl3, cm−1) 2969, 1613, 1501, 1138. Anal. Calcd for C22H23O2ClS: C, 68.29; H, 5.99. Found: C, 68.53; H, 6.00.

Provenance & Evidence