1,3-Propanediol → HCID 53853402, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(3-fluorophenylsulfonyloxy)-5-methylphenol (930 mg, 3.3 mmol, as prepared in the preceding step), 1,3-propanediol (0.75 mL, 10 mmol), 1,1'-(azodicarbonyl)dipiperidine (1.76 g, 7.0 mmol), and anhydrous tetrahydrofuran (20 mL) was cooled to 0° C. under nitrogen. Tri-n-butylphosphine (1.7 mL, 7.0 mmol) was added dropwise over 8.5 minutes. The mixture was stirred at 0° C. for 5 minutes then at ambient temperature for 5.5 hours. Diethyl ether (100 mL) was added, and the mixture was stirred for 15 minutes. The mixture was filtered, and the filtrate was concentrated. The residue was purified by flash column chromatography through silica gel (25% to 35% ethyl acetate in hexane) to give the title compound as a yellow oil (877 mg, 78%). 1H-NMR (300 MHz, CDCl3) δ 7.65-7.68 (m, 1H), 7.50-7.60 (m, 2H), 7.35-7.41 (m, 1H), 6.63 (br s, 1H), 6.41 (br s, 1H), 6.38 (br t, 1H, J=2.1 Hz), 4.01 (t, 2H, J=6.0 Hz), 3.82 (br t, 2H, J=6.0 Hz), 2.25 (s, 3H), 1.99 (pentet, 2H, J=6.0 Hz). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C16H17FO5S: 363.1 (M+Na), 379.0 (M+K). Found: 362.8, 378.9.

Provenance & Evidence