Iodine → (E)-10-Iodo-2-(phenylmethylidene)deca-3,9-diyn-1-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of iodine (1.479 g, 5.83 mmol) in toluene (80 mL) was added morpholine (1.354 g, 15.54 mmol) followed by heating at 60° C. for 30 minutes. To the resultant mixture was added a solution of Compound 3 (462.3 mg, 1.94 mmol) in toluene (10 mL) and the mixture was heated at the same temperature for 6 hours. The reaction mixture was then allowed to cool down to room temperature and purified, without aqueous work up, by flash column chromatography (silica gel, 100 percent hexane and then 17 percent EtOAc in hexane) to give 630.3 mg (89 percent) of Compound 4: yellow oil; Rf=0.17 (17 percent EtOAc in hexane); IR (neat) 3362 (br), 2942, 2860, 2210, 1446, 1072 cm−1; 1H NMR (300 MHz, CDCl3) δ7.83-7.79 (m, 2H), 7.37-7.24 (m, 3H), 6.71 (s, 1H), 4.26 (d, J=1.20 Hz, 2H), 2.51-2.39 (m, 4H), 1.95 (br s, 1H), 1.76-1.62 (m, 4H); 13C NMR (75 MHz, CDCl3) δ136.7, 133.5, 129.1, 128.9, 128.8, 122.5, 98.7, 94.7, 79.4, 68.2, 28.3, 28.1, 21.0, 20.1, −5.9; MS (+CI) m/z (relative intensity) 365 (M+H+, 10), 220 (100); HRMS (+EI) calcd for C17H17IO 364.0324 (M+), found 364.0299.

Provenance & Evidence