Nitrogen → (3-(2-Methyl-[1,3]dioxolan-2-yl)-phenyl)methyl methanesulfonate

Participants

Reaction Conditions

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [3-(2-methyl-[1,3]dioxolan-2-yl)-phenyl]-methanol (1.68 g, 8.65 mmol) in dry CH2Cl2 (20 mL) was treated at 0° C. with Et3N (1.60 mL, 11.38 mmol) followed by DMAP (109 mg, 0.88 mmol) and Ms-Cl (0.80 mL, 10.13 mmol). After stirring at 0° C. for 0.5 h, the reaction was quenched with water (10 mL). The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. The crude residue was purified by FC (hept-EA 9:1 to 0:1) to give pure (3-(2-methyl-[1,3]dioxolan-2-yl)-phenyl)methyl methanesulfonate as a white solid. Part of this material (300 mg, 1.10 mmol) was dissolved in dry DMF (5 mL) and treated with NaN3 (220 mg, 3.35 mmol) at 80° C. until completion of the reaction. The reaction mixture was then cooled down to rt and partitioned between EA and water. The layers were separated and the org. layer dried over MgSO4, filtered and concentrated under reduced pressure to give crude 3-(azidomethyl)-(2-methyl-[1,3]dioxolan-2-yl)benzene as a yellow oil. LC-MS-conditions 02: tR=0.99 min.

Provenance & Evidence