4-Bromobenzaldehyde → 4-(5-Phenoxypentyl)benzyl alcohol

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Reaction Steps

4-(5-Phenoxypent-1-ynyl)benzaldehyde--By the method of C. D. Perchonock, et al., J. Med. Chem., 29, 1442 (1986), 2.0 g 4-bromobenzaldehyde, 2.1 g (0.013 mole) 5-phenoxypent-1-yne, 0.76 g bis (triphenylphosphine) palladium (II) chloride, and 0.10 g copper (I) iodide in 7.0 mL dry triethylamine were stirred under argon for 17 hours. The mixture was diluted with ethyl acetate and washed with 2% H2SO4, then with water and finally with saturated aqueous NaCl. The resultant dark solution was treated with about 2 g activated carbon powder, dried over MgSO4 and then filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography using 3-6% ethyl acetate in hexane as eluant. The title compound was obtained as a tan solid (2.2 g, 78%).

Provenance & Evidence