Triphenylphosphine → HCID 70079702, compound

Participants

Reaction Steps

To a solution of the product of step B (1.52 g, 5.47 mmol) in 15 mL of MeOH:THF (2:1) was added 1H NaOH (5.9 mL, 5.9 mmol) and the reaction stirred at room temperature for 1.5 hours. The reaction was diluted with water and washed with Et2O. The aqueous phase was acidified with 1H NaHSO4, extracted with EtOAc, dried (MgSO4), filtered and evaporated under reduced pressure. The residue and Ph3P (1.86 g, 7.11 mmol) was immediately dissolved in dry THF (20 mL) and cooled to -40° C. Neat diethyl azodicarboxylate (1.27 g, 7.42 mmol) was added dropwise via syringe and the solution stirred at -40° C. for 3 hours. Concentration of the solvent under reduced pressure and silica gel chromatography (EtOAc:hexane 4:6) of the residue afforded 1.05 g (69%) of the title product as a colorless oil. NMR spectrum analysis indicated the product was contaminated with -10% of the trans isomer. 1H-NMR (300 MHz, CDCl3) δ 1.25-1.80 (m, 7H), 1.90-2.00 (m, 1H), 2.24 (dd, J=11Hz, J=17 Hz, 1H), 2.55-2.79 (m, 4H), 4.30 (m, 1H) 5.02-5.14 (m, 2H), 5.66-5.80 (m, 1H), 7.27 (d, J=8 Hz, 2H), 7.57 (d, J=8 Hz, 2H).

Provenance & Evidence