Hexane → Ammonium Hydroxide

Participants

Reaction Steps

9.9 ml (13.9 mmol) of a 1.4 M solution of n-butyllithium in hexane were added dropwise, under a nitrogen atmosphere and at room temperature, to a suspension of 5.4 g (13.9 mmol) of benzyltriphenylphosphonium chloride in 30 ml of dry THF. The reaction mixture was stirred for 1 h, then a solution of 1 g (3.5 mmol) of (±)-trans-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-ethyl-4a-(3-methoxyphenyl)-6-isoquinolinone in 10 ml of dry THF was added. The reaction mixture was refluxed 4 h, then cooled and poured onto water and the aqueous phase was extracted with AcOEt. The organic phase was dried over Na2SO4 and the solvent removed in vacuo. The crude reaction mixture was purified by flash chromatography, eluting with a mixture CH2Cl2 /MeOH/conc. NH4OH 90:7:0.7 respectively, yielding 0.94 g of the title compound.

Provenance & Evidence