Triphenylphosphine → 2-(1-Azidoethyl)-3-phenylbenzo[b]thiophene

Participants

Reaction Steps

DIAD (556 mg, 2.75 mmol) was added to a solution of triphenylphosphine (722 mg, 2.75 mmol) in dioxane (5 mL) at 0° C. under a nitrogen atmosphere. After 10 min stirring, 1-(3-phenylbenzo[b]thiophen-2-yl)ethanol (350 mg, 1.37 mmol) was added followed by diphenylphosphoryl azide (454 mg, 1.65 mmol). Stirring at 20° C. was continued for 16 h and then volatiles were concentrated in vacuo. The crude reaction mixture was purified by column chromatography (Si—PCC, gradient 0-20% DCM in cyclohexane) affording 2-(1-Azidoethyl)-3-phenylbenzo[b]thiophene as a colourless oil (211 mg, 55%). 1H NMR (CDCl3, 400 MHz): δ 7.88 (1H, d, J=7.87 Hz), 7.54-7.42 (4H, m), 7.41-7.29 (4H, m), 4.97 (1H, q, J=6.80 Hz), 1.58 (3H, d, J=6.80 Hz).

Provenance & Evidence