N-Hydroxyphthalimide → HCID 14814229, compound

Participants

Reaction Steps

To a solution of (R)-1,4-dibenzyloxy-2-hydroxybutane (8 g, 28 mmol) in dry tetrahydrofuran (150 ml) was added triphenylphosphine (11 g, 42 mmol) and N-hydroxyphthalimide (6.8 g, 42 mmol). The solution was treated dropwise with diethyl azodicarboxylate (6.6 ml, 42 mmol). A dark red colouration appeared, gradually fading and the solution became warm. The solution was stirred at room temperature for 16 hours, then treated with additional triphenyl phosphine (2.25 g, 8.5 mmol) N-hydroxyphthalimide (1.35 g, 8.5 mmol) and diethyl azodicarboxylate (1.35 ml, 8.5 mmol). After stirring for an additional 24 hours at room temperature, the solvent was removed under reduced pressure and the residue dissolved in ethyl acetate-hexane 1:1 (100 ml) and refrigerated. A white solid crystallised out and was filtered off. The solution was evaporated to dryness and the residue dissolved in ethyl acetate-hexane 1:1 (50 ml) and refrigerated. After filtration, the filtrate was evaporated to dryness and the residue chromatographed on silica, eluting with ethyl acetate-hexane 1:2 to give (S)-N-(1,4-dibenzyloxybut-2-oxy)phthalimide (11 g, (91%), [α]25 -17.4° (c 0.8 in ethanol); IR: υmax

Provenance & Evidence