Potassium Carbonate → 2-{[2-({4-[(4-Fluorophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}oxy)ethyl]oxy}ethanol

Participants

Reaction Steps

The O-alkylation procedure described for 10 (Example 5, step 2) was followed using 9 (339 mg, 1 mmol), K2CO3 (414 mg, 3 mmol), 2-[(2-chloroethyl)oxy]ethanol (0.63 mL, 6 mmol), and acetone (30 mL). The reaction mixture was refluxed for 60 h. The reaction mixture was filtered, concentrated, and purified by column chromatography to give 190 mg (45%) of the title product 24 as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.16-7.13 (m, 2H), 7.11-7.07 (m, 2H), 7.0 (d, J=8.4 Hz, 2H), 6.84 (d, J=8.4 Hz, 2H), 4.59 (t, J=5.2 Hz, 2H), 4.03 (t, J=4.8 Hz, 2H), 3.70 (t, J=4.4 Hz, 2H), 3.49-3.44 (m, 4H), 1.90 (s, 2H), 1.86 (s, 2H), 1.24 (s, 2H), 0.87 (s, 6H), 0.87 (s, 6H). LCMS (APCI): m/z 427 (M+H)+.

Provenance & Evidence