Diphenylphosphine → HCID 19594736, compound

Participants

Reaction Steps

Add n-butyl-lithium (4.80 mL, 0.012 mole) in THF (60 mL) dropwise to diphenylphosphine (Ph2PH, 2.34 g, 0.012 mole) at -20° C. Warm to resulting red solution to abient temperature, then stir for 30 minutes. Prepare a solution of 5-methoxy-2-propoxy-fluoren-9-one (0.88 g, 3.3 mmole) in THF (20 mL) and add to the stirred dark-red Ph2PH solution, stirring for an additional hour while the color changes from dark-red to brown, then heating at reflux for 15 minutes. Cool to abient temperature, then quench with a saturated solution of NH4Cl. Separate the THF layer, wash with brine, dry over MgSO4, filter and concentrate the filtrate to an orange oil. Dissolve the oil in CH2Cl2 and extract with 5% aq. NaOH (50 mL) as a purple solid formed in the aqueous layer.

Provenance & Evidence