Diisopropyl Azodicarboxylate (40% in Toluene, ca. 1.9mol/L)

• 3-Phenyl-1-propanol [P0214]
• 5-Mercapto-1-phenyl-1H-tetrazole [P0640]
• Diisopropyl Azodicarboxylate (= DIAD) (40% in Toluene, ca. 1.9mol/L) [A1246]
• Triphenylphosphine [T0519]
• Tetrahydrofuran (= THF) Anhydrous (stabilized with BHT) [T2394]

To a solution of triphenylphosphine (0.88 g, 3.4 mmol), 5-mercapto-1-phenyl-1H-tetrazole (0.79 g 4.4 mmol), 3-phenylpropan-1-ol (0.30 g, 2.2 mmol) in anhydrous tetrahydrofuran (22 mL) was added DIAD (40% in toluene, 2.1 mL, 4.0 mmol) at 0 °C and the mixture was stirred at rt for 1 hour. The solution was dropped into water (40 mL). The mixture was extracted with ethyl acetate (40 mL x 3), and organic phase was dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by column chromatography (ethyl acetate:hexane = 1:9 on silica gel) to give 1 (0.68 g, quant) as a white solid.

The reaction mixture was monitored by TLC (ethyl acetate:hexane = 1:9, Rf = 0.29).

Compound 1

¹H NMR (400 MHz, CDCl₃); δ 7.63-7.50 (m, 5H), 7.35-7.26 (m, 2H), 7.23-7.14 (m, 3H), 3.40 (t, J = 7.0 Hz, 2H), 2.79 (t, J = 7.6 Hz, 2H), 2.18 (quin, J = 7.3 Hz, 2H)

• One-Pot Substitution of Aliphatic Alcohols Mediated by Sulfuryl Fluoride
• J. Y. Mo, M. Epifanov, J. W. Hodgson, R. Dubois, G. M. Sammis, Eur. J. Org. Chem. 2020, 26, 4958.