Diethyl Ether → HCID 9818417, compound

Participants

Reaction Steps

In a 10 mL oven-dried flask charged with Mg turnings (0.12 g, 4.9 mmol) which was activated under vacuum by the use of a heat-gun. Under inert atmosphere was added a suspension of 1-bromo-2-ethylbenzene (0.66 g, 3.6 mmol) in Et2O (2 mL) and the reaction mixture was allowed to reflux for 2 hours. A suspension of compound 4 (0.50 g, 2.4 mmol) in CH2Cl2 (2 mL) was added via a syringe and the reaction mixture was stirred at rt overnight. The reaction mixture was quenched by addition of H2SO4 (14 mL, 2 M) and stirred at rt for 2 hours followed by addition of NaOH (20 mL, 2 M). Addition of THF (20 mL) was followed by extraction with ethyl acetate (3×50 mL) and the combined organic phases are washed with brine (10 mL) and NaOH (10 mL, 2 M), and the organic phases were dried (MgSO4) and evaporated to dryness to produce 0.75 g of crude 21. The crude product was subjected to CC [eluent: CH2Cl2: MeOH (99:1)] to give pure 21 (0.68 g, 90%); LC-MS [M+H]+ 315 (cald. 315.5).

Provenance & Evidence