Triethylamine → HCID 23294309, compound

Participants

Reaction Steps

3-(4-Benzyloxyphenyl)prop-1-yl mesylate. To a solution of 3-(4-benzyloxyphenyl)propan-1-ol (9.76 g, 40 mmol) in 75 mL of methylene dichloride and 7.8 mL of triethylamine was added dropwise methanesulfonyl chloride (9.17 g, 80 mmol) at -20° C. The resulting mixture was allowed to stir at rt for 30 min. and was diluted with 100 mL of methylene dichloride. The solution was washed with 1M HCl (2×100 mL), saturated sodium bicarbonate solution (100 mL) and brine (50 mL), then was dried over MgSO4. Evaporation of solvent gave 12.2 g (95%) of the crude title compound as a white solid. 1H NMR (CDCl3) 2.042 (t, J=6.6 Hz, 2 H), 2.694 (t, J=7.5 Hz, 2 H), 2.984 (s, 3 H), 4.195 (t, J=6.0 Hz, 2 H), 5.045 (s, 2 H), 6.928 (d, J=8.4 Hz, 2 H), 7.116 (d, J=8.4 Hz, 2 H), 7.418 (m, 5 H).

Provenance & Evidence