(+)-Benzyl glycidyl ether → HCID 11117222, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2S)-2-[(benzyloxy)methyl]oxirane (50 g, 305 mmol) in THF (1500 mL) at 0° C. was added copper bromide (4.37 g, 30.5 mmol). The resulting solution was stirred at 0° C. for 10 minutes and allylmagnesium bromide (1M in THF, 335 mL, 335 mmol) was added. The reaction was stirred for 2 hours at 0° C. and then quenched at 0° C. with saturated aqueous NH4Cl and diluted with DCM. The mixture was stirred at ambient temperature for 20 minutes and filtered to remove insoluble material. The filtrate was extracted with DCM (3×) and the combined organic phases were dried over MgSO4, filtered, and concentrated in vacuo. Flash column chromatography eluted with 10 to 40% EtOAc/hexanes provided (2S)-1-(benzyloxy)hex-5-en-2-ol. 1H NMR (400 MHz, CDCl2): δ 7.37-7.26 (m, 5 H); 5.88-5.74 (m, 1 H); 5.08-4.93 (m, 2 H); 4.54 (s, 2 H); 3.83 (s, 2 H); 3.53-3.44 (m, 1 H); 3.33 (dd, J=9.1, 8.2 Hz, 1 H); 2.49 (s, 1 H); 2.30-2.00 (m, 2 H); 1.64-1.39 (m, 2 H).

Provenance & Evidence