Diethyl Ether → HCID 19739547, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (55) (442 mg, 1 mmol) in MeOH (20 mL), was added LiOH (10 equiv). The resulting mixture was refluxed for 12 hours and then allowed to cool to 25° C. The reaction mixture was poured into a saturated solution of NH4Cl (50 mL) and Et2O (70 mL). The organic layer was separated, dried (MgSO4) and concentrated by rotary evaporation to yield 17) (349 mg, 90%) as a yellow oil; 1H NMR (CDCl3) δ 9.00 (s, 1 H), 7.30 (d, J=7.8 Hz, 2H), 7.18 (d, J=7.8 Hz, 2 H), 4.60 (s, 2 H), 2.94 (t, J=7.8 Hz, 2 H), 2.66 (t, J=7.5 Hz, 2 H), 2.23 (t, J=6.9 Hz, 2 H), 1.52 (s, 6 H), 1.28 (m, 16 H), 0.89 (t, J=6.9 Hz, 3 H); 13 ; C NMR (CDCl3) δ 179.25, 139.24, 137.31, 128.17, 128.08, 84.85, 82.37, 70.79, 6.06, 35.89, 31.89, 30.36, 29.55, 29.32, 29.24, 29.11, 28.82, 28.78, 22.68, 18.60, 14.13. ##STR31##

Provenance & Evidence