Benzyl Alcohol → HCID 23589540, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of Example 84 (36 mg, 0.12 mmol) in 1,4-dioxane (1.4 mL) under argon with powdered 4 Å molecular sieves was added triethylamine (19 μL, 0.14 mmol, 1.2 eq) and diphenylphosphoryl azide (30 μL, 0.14 mmol). The mixture was heated at 85° C. for 1 hr and then benzyl alcohol (24 μL, 0.23 mmol) was added. The reaction mixture was warmed at 85° C. for 15 hrs. The mixture was filtered, concentrated in vacuo, and purified directly by rotary chromatography directly on a 1 mm silica gel plate eluting with 2% methanol in chloroform to provide 29 mg (60%) of yellow oil. MS: [M+H]+=419.2; 1H NMR (CDCl3): δ 8.27 (d, J=2.7 Hz, 1H), 7.98 (s, 1H), 7.95 (dd, J=8.8, 2.7 Hz, 1H), 7.90 (s, 1H), 7.43-7.35 (m, 5H), 6.81 (d, J=8.8 Hz, 1H), 6.46 (br s, 1H), 5.24 (s, 2H), 3.96 (s, 3H), 2.82 (q, J=7.7 Hz, 2H), 1.34 (t, J=7.7 Hz, 3H).

Provenance & Evidence