Triphenylphosphine → HCID 11233520, compound

Participants

Reaction Steps

A solution of triphenylphosphine (0.438 g, 1.67 mmol) in 10 mL of THF is cooled to −78° C. and DIAD (0.430 g) is added in one portion. (3-Hydroxy-propyl)-carbamic acid tert-butyl ester (560 mg, 1.3 eq) in 1 mL of THF is added and the solution is allowed to warm to room temperature over the course of 1 hr. The yellow solution is treated with 5-chloro-4-hydroxycoumarin (0.300 g, 1.5 mmol) and is stirred at ambient temperature for 3.5 hrs. The solvent is removed under reduced pressure and the crude product is purified using an ISCO 4 g SiO2 column eluting with ether/heptane gradient to afford the title compound (0.106 g, 20%). 1H NMR (CDCl3, 300 MHz) δ 7.27 (3H, m), 5.71 (1H, s), 4.73 (1H, brs), 4.17 (2H, t, J=5.75 Hz), 3.41 (2H, q, J=6.5 Hz), 2.13 (2H, m), 1.43 (9H, s); MS (ESI, Pos.) calcd for C17H20ClNO5 m/z [M+H+Na]=376.1, found 376.1.

Provenance & Evidence