Triphenylphosphine → trans-4-[4-(Tert-butoxycarbonyl)phenoxy]-2-butene

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A solution of 1,1-dimethylethyl 4-hydroxybenzoate (3.68 g, 18.9 mol) and 2-buten-1-ol (1.37 g, 18.9 mol) in dry benzene (100 ml) at 22° C. was treated with triphenylphosphine (5.48 g, 20.9 mmol) followed by a solution of diisopropyl azodicarboxylate (4.22 g, 20.9 mmol) in dry benzene (10 ml) added dropwise over 7 minutes. After 3 hours at 22° C., the solvent was concentrated under reduced pressure and the residue was chromatographed on silica gel. Elution with a mixture of toluene and ethyl acetate (99:1) gave 3.70 g (79%) of the title material as a clear oil: bp 85-90° C./0.1 torr (bulb to bulb, air bath temperature).

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