Ethylene Glycol → HCID 23294929, compound

Participants

Reaction Steps

2-(Diisopropylamino)ethyl 1-phenyl-4-oxocyclohexanecarboxylate hydrochloride (3 mmol), prepared in Example 119, was refluxed for 4 h with p-toluenesulfonic acid (1.5 mmol) and ethyleneglycol (4 mmol) in toluene (50 mL) using a Dean-Stark trap. The reaction mixture was partitioned between Et2O and 2 M NaHCO3. The organic layer was dried (Na2SO4) and evaporated. The residue was dissolved in Et2O and HCl (g)/Et2O was added. The amine salt was recrystallized from acetone/Et2O to yield 0.53 g (43%); mp 121-128° C.; 1H NMR (CD3OD) δ 1.25 (d, 12H), 1.72 (m, 4H), 2.13 (m, 2H), 2.47 (m, 2H), 3.35 (t, 2H), 3.59 (m, 2H), 3.93 (m, 4H), 4.42 (t, 2H), 7.26-7.47 (m, 5H).

Provenance & Evidence