4-Pentyn-1-ol → HCID 69286085, compound

Participants

Reaction Conditions

Reaction Steps

See Fancelli D.; Fagnola, M. C.; Bedeschi, A. Solid phase Synthesis of 2-Substituted Benzofurans via the Palladium-catalyzed Heteroannulation of acetylenes. Tetrahedron Letters 1997, 38, 2311-2314. A mixture of methyl 4-hydroxy-3-iodobenzoate (93) (35 g, 125.9 mmol), 4-pentyn-1-ol (11.00 g, 130.7 mmol) and copper (I) oxide (12.62 g, 88.2 mmol) in dyr pyridine (150 mL) was stirred at 100-120° C. overnight. The mixture was allowed to cool to room temperature, diluted with EtOAc (200 mL), filtered through a Celite pad (5 cm) and concentrated. The residue was dissolved in EtOAc (300 mL), washed with 2 M HCl (50 mL), brine (100 mL), dried over Na2SO4, filtered and concentrated. Column chromatography (SiO2, EtOAc/hexanes, 1/1) followed by recrystallization (hexanes/diethyl ether, 2/1) afforded 95 as light yellow crystals (14.39 g, 49%). 1H NMR (DMSO-d6) δ8.20 (s, 1H), 7.86 (d, J=8.2 Hz, 1H), 7.13 (d, J=8.2 Hz, 1H), 6.74 (s, 1H), 4.59 (b, 1H), 3.49 (b, 2H), 3.86 (s, 3H), 2.84 (t, J=7.1 Hz, 2H), 1.85 (m, 2H). HPLC (method B) tR 4.20 min (100.00 area %).

Provenance & Evidence