1,3-Propanediol → HCID 54004475, compound

Participants

Reaction Steps

To a cooled (0° C.) solution of 0.815 g (2.37 mmol) 3-(3-bromophenylsulfonyloxy)-5-methylphenol, as prepared in the preceding step, 0.51 mL (7.12 mmol) of 1,3-propanediol and 1.20 g (4.75 mmol) of 1,1'-(azodicarbonyl)dipiperidine in 15 mL of anhydrous tetrahydrofuran was added 1.18 mL (4.75 mmol) of tri-n-butylphosphine dropwise over 8 min. Dichloromethane (10 mL) was added to aid stirring. After stirring at ambient temperature for 5.5 h, the reaction mixture was diluted with 100 mL of diethyl ether. The resulting mixture was stirred for 30 min, filtered and the filtrate concentrated to give a pale yellow semisolid. This residue was flash chromatographed on 80 g of silica gel with 25-50% ethyl acetate-hexane to afford 0.914 g (96% yield) of the title compound as a colorless resin: 1H-NMR (300 MHz; CDCl3) δ 8.01 (t, 1H, J=1.8 Hz), 7.79 (m, 2H), 7.42 (t, 1H, J=8.0 Hz), 6.64 (s, 1H), 6.41 (s, 1H), 6.37 (t, 1H, J=2.2 Hz), 4.01 (t, 2H, J=6.0 Hz), 3.83 (t, 2H, J=5.6 Hz), 2.26 (s, 3H) and 2.00 (m, 2H).

Provenance & Evidence