Triphenylphosphine → 4-(4-tert-butoxyphenoxy)tetrahydro-2H-pyran

Participants

Reaction Steps

4-Tert-butoxyphenol (200 mg, 1.203 mmole) and PPh3 (410 mg, 1.564 mmole) were combined in toluene (5 mL). To this was added tetrahydro-2H-pyran-4-ol (0.149 mL, 1.564 mmole). DIAD (0.304 mL, 1.564 mmole) was added dropwise at RT. After stirring overnight the mixture was concentrated. Flash column chromatography (Biotage-SNAP-25 g SiO2, 10% EtOAc/hexanes) gave 4-(4-tert-butoxyphenoxy)tetrahydro-2H-pyran (257 mg, 85%) as a clear oil. 1H NMR (400 MHz, CDCl3): 06.90 (d, J=8.9 Hz, 2 H); 6.83-6.79 (m, 2 H); 4.39 (m, 1 H); 4.03-3.95 (m, 2 H); 3.56 (m, 2 H); 2.04-1.96 (m, 2 H); 1.83-1.72 (m, 2 H); 1.30 (s, 9 H).

Provenance & Evidence