Methyl iodide → Tert-butyl methyl(pent-4-yn-1-yl)carbamate

Beteiligte Stoffe

Reaktionsschritte

A 500 mL round bottom flask was charged with pent-4-ynyl-carbamic acid tert-butyl ester (5.0 g, 27.3 mmol) and tetrahydrofuran (138 mL) and the resulting mixture cooled with an ice/water bath. Sodium hydride (830 mg, 32.9 mmol) was added in 3 portions and the resulting mixture stirred at room temperature for 20 minutes. Methyl iodide (8.6 mL, 138.1 mmol) was slowly added and the resulting mixture stirred for 72 h. The resulting mixture was diluted with dichlormethane (350 mL), washed with 1N HCl (100 mL), 1N, NaOH (100 mL), and water (100 mL). The organic layer was washed with MgSO4, filtered, then concentrated in vacuo to yield methyl-pent-4-ynyl-carbamic acid tert-butyl ester. 1H NMR (300 MHz, CDCl3) δ 3.31 (t, J=7.0 Hz, 2H), 2.86 (s, 3H), 2.17-2.24 (m, 2H), 1.96 (s, 1H), 1.72-1.79 (m, 2H), and 1.46 (s, 9H).

Herkunft & Nachweise