Methyl iodide → HCID 68668293, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (2S)-1-(benzyloxy)hex-5-en-2-ol (71 g, 344 mmol) in DMF (500 mL) at 0° C. was added sodium hydride (16.52 g, 413 mmol) in portions over 30 minutes. The resulting suspension was stirred at 0° C. for 15 minutes and then at ambient temperature for 15 minutes. The mixture was cooled to 0° C. and methyl iodide (43 mL, 688 mmol) was added. The reaction mixture was stirred at ambient temperature overnight. The mixture was cooled to 0° C. and quenched with water. The mixture was extracted with DCM (3×). The organic layers were combined and washed with water (2×), dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was used in the next reaction without further purification. 1H NMR (400 MHz, CDCl2): δ 7.34 (s, 5 H); 5.85-5.74 (m, 1 H); 5.06-4.89 (m, 2 H); 4.55 (s, 2 H); 3.49 (d, J=4.7 Hz, 2 H); 3.41 (s, 3 H); 3.37 (m, 1 H); 2.16-2.04 (m, 2 H).

Provenance & Evidence