p-Toluenesulfonic acid → N-{3-[5-(4-Benzyloxyphenoxy)-[1,3]dioxan-2-yl]propyl}acetamide

Participants

Reaction Steps

2-(4-Benzyloxyphenoxy)propane-1,3-diol (98 mg, 0.36 mmol), N-(4,4-diethoxybutyl)acetamide (73.06 mg, 0.36 mmol) and p-toluenesulfonic acid (61.89 mg, 0.36 mmol) were stirred in 6 ml of toluene at 60° C. for 2 h and concentrated. The organic phase was separated off, concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 30.8 mg (22%) of cis-N-{3-[5-(4-benzyloxyphenoxy)-[1,3]dioxan-2-yl]propyl}acetamide, M+H+: 386.15 and 29.8 mg (22%) of trans-N-{3-[5-(4-benzyloxyphenoxy)-[1,3]dioxan-2-yl]propyl}acetamide, M+H+: 386.19.

Provenance & Evidence