Water → Cis-1-[4-(benzoxazol-2-yl)benzyloxy]-2-triphenylmethylaminocyclohexane

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Reaction Steps

Cis-2-triphenylmethylaminocyclohexanol (1.52 g; 4.25 mmol) is added to a solution of sodium hydride (256 mg; 60%; 6.4 mmol) in 20 ml dry THF and refluxed overnight. The solution is cooled, 4-(benzoxazol-2-yl)benzyl bromide (1.3 g; 4.5 mmol) is added in one portion and refluxed for 5 hrs. This is then poured into water and extracted with 2×100 ml CH2Cl2, dried (Na2SO4), concentrated to dryness and flash chromatographed using 4:1 8:1; hexane:EtOAc to obtain Cis-1-[4-(benzoxazol-2-yl)benzyloxy]-2-triphenylmethylaminocyclohexane which is used directly in the next step.

Provenance & Evidence