Triphenylphosphine → HCID 57791770, compound

Participants

Reaction Steps

Pyridin-4-ol (6.0 g, 63.09 mmol), cyclobutanol (5.00 g, 69.40 mmol) and triphenylphosphine (18.20 g, 69.40 mmol) were added to THF (250 mL) and stirred for 10 minutes. To this was slowly added diisopropylazodicarboxylate (13.49 mL, 69.40 mmol). Once the addition was complete the reaction was stirred at 50° C. for 1 hour. The solvent was evaporated and the crude residue was dissolved in diethyl ether. To this was added a small amount of triphenylphoshine oxide and the reaction was stirred for 30 minutes to afford a solid, this was filtered and discarded. The solvent was evaporated and the pale yellow gum was acidified with 2.0M HCl, extracted with diethyl ether (1×75 mL) and the aqueous was then basified with solid potassium hydroxide. This was then extracted with diethyl ether (3×75 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford yellow gum. This was purified by distillation at 0.60 mBar, collecting fractions that distilled at 80° C. to afford the desired compound as a colourless oil (4.70 g, 49.9%); 1H NMR (400.132 MHz, CDCl3) δ 1.78-1.66 (1H, m), 1.95-1.86 (1H, m), 2.24-2.14 (2H, m), 2.51-2.43 (2H, m), 4.69 (1H, quintet), 6.70 (2H, d), 8.40 (2H, d); m/z (LC-MS, ESI+), RT=1.76 (M+H 150).

Provenance & Evidence