Triphenylphosphine → HCID 178473588, compound

Participants

Reaction Steps

A solution of D-2 (304 mg) and triphenylphosphine (524 mg) in dry THF (5 ml) is stirred at room temperature under argon and DEAD (0.32 ml, 4 mmole) is added via syringe. The solution warms upon addition of DEAD and is allowed to cool to 20°-25° over a period of 30 min. The reaction mixture is concentrated in vacuo, and the residue chromatographed on silica gel (elution with ethyl acetate/hexane, 1:2) to deliver D-3 as a solid, m.p. 96.5-97.5° (hexane/diethyl ether): [α]D25 -76.2° (c 0.795, MeOH); IR (cm-1, mull) 3348, 2951, 1797, 1792, 1682, 1537, 1250, 1176; PMR (80 MHz, CDCl3 δ) 4.55-4.17, 4.17-3.60, 3.78, 2.60, 2.56, 1.88-1.09, 1.43, 0.94; MS (Cl, NH3, m/z) 248, 304, 204, 266, 305.

Provenance & Evidence