Triphenylphosphine → HCID 57791810, compound

Participants

Reaction Conditions

Reaction Steps

Di-tert-butyl azodicarboxylate (719 mg, 3.12 mmol) was added in one portion to pyridin-4-ol (YY) (297 mg, 3.12 mmol), 1,3-difluoropropan-2-ol (100 mg, 1.04 mmol) and Polymer supported triphenylphosphine (1.89 mmol/g; 1016 mg, 3.12 mmol) in dichloromethane (10 mL) at 20° C. under air. The resulting suspension was stirred at 20° C. for 4 hours. The mixture was filtered and the solvent evaporated to a yellow oil. The reaction mixture was diluted with dichloromethane (25 mL), and washed sequentially with 2M NaOH (2×10 mL) and saturated brine (10 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. This was re-dissolved in dichloromethane (25 mL), and washed with 2M HCl (10 mL). The aqueous layer was basified with 2M NaOH and extracted with dichloromethane (×3). The combined organic layers were dried over MgSO4, filtered and evaporated to afford the desired compound as a viscous oil (90 mg, 50%); 1H NMR (400.132 MHz, CDCl3) δ 4.60-4.67 (2H, m), 4.71-4.76 (2H, m), 4.78-4.90 (1H, m), 6.92 (2H, d), 8.48 (2H, d); m/z (LC-MS, ESI+), RT=1.53 (M+H 174).

Provenance & Evidence