4-Bromophenol → HCID 178419399, compound

Participants

Reaction Conditions

Reaction Steps

4-Bromophenol (0.344 g, 2.0 mmol) was added to a solution of (+/−)-[cis-4-(tetrahydro-2H-pyran-2-yloxy)cyclohexyl]methanol (0.387 g, 1.81 mmol) in THF (10 mL). Triphenylphosphine (0.474 g, 1.81 mmol) and triethylamine (0.183 g, 1.81 mmol) were added. The resulting solution was cooled to 0° C. and DIAD (0.365 g, 1.81 mmol) was added by dropwise addition. After 18 hours the reaction was quenched by addition of water and extracted with ether (2×100 mL). The organic layers were combined and washed with 1N NaOH (2×100 mL) then water (2×100 mL). The organic layer was dried (MgSO4), filtered and concentrated to give a clear oil. Purification by flash column chromatography on a Biotage SNAP cartridge Kp-sil 100g column (hexanes/ethyl acetate 9:1) afforded the title compound as a white solid (324 mg, 48%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.41-1.75 (m, 11 H) 1.75-1.98 (m, 4 H) 3.39-3.54 (m, 1 H) 3.70-3.80 (m, 2 H) 3.83-3.97 (m, 2 H) 4.55-4.69 (m, 1 H) 6.66-6.82 (m, 2H) 7.29-7.42 (m, 2 H).

Provenance & Evidence