Tetrahydrofuran → HCID 59238593, compound

Participants

Reaction Steps

A mixture of 1,4-cyclohexanedione monoethylene acetal (7.81 g, 50.00 mmol), morpholine (4.81 mL, 55 mmol) and 1H-1,2,3-triazole (3.48 mL, 60 mmol) in toluene (50 mL) was refluxed for 6 hours while collecting water using a Dean-Stark apparatus. The white suspension containing 10 was allowed to cool to RT and added dropwise over 1 hour to a cooled (ice/salt/water bath) 3.0 M MeMgCl solution in THF (66.67 mL, 200 mmol) while maintaining the internal temperature <24° C. The reaction mixture was stirred at RT for a further 2 h. The mixture was then diluted with Et2O (500 mL). An aqueous solution of NH4Cl was added in portions until a precipitate formed. The organic layer was decanted off, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by SGC on amino silica (Chromatorex NH, Fuji Silysia) using hexane:EtOAc as eluent (gradient elution from 100:0 to 50:50, v/v) to give 11 (10.94 g, 91%) as a yellowish white solid. 1H NMR (400 MHz, CDCl3) δ 0.89 (s, 3H), 1.41-1.48 (m, 4H), 1.80-1.94 (m, 4H), 2.50 (t, J=4.2 Hz, 4H), 3.70 (t, J=4.6 Hz, 4H), 3.95 (app. t, J=1.7 Hz, 4H).

Provenance & Evidence