反应详情

温度

-78 °C

To a solution of 3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (200 mg, 0.86 mmol) in THF (3 ml) under N2 at −78° C. is added, dropwise, a 1.8 M solution of lithium diisopropylamine in tetrahydrofuran/heptane/ethylbenzene (0.53 ml, 0.95 mmol). The resulting solution is allowed to stir at −78° C. for 40 minutes. A solution of 4-fluorobenzyl bromide (0.16 ml, 1.3 mmol) in THF (1 ml) is then added in one portion, the reaction mixture is stirred at −78° C. for 30 minutes before being allowed to warm to room temperature over a period of 60 minutes. The reaction is quenched by the addition of saturated aqueous ammonium chloride (5 ml) and extracted with ethyl acetate (2×10 ml). The combined organics are purified by flash chromatography to give 5-(4-fluoro-benzyl)-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (236 mg).

1. stirringthe reaction mixture is stirred at −78° C. for 30 minutes
2. temperatureto warm to room temperature over a period of 60 minutes
3. customThe reaction is quenched by the addition of saturated aqueous ammonium chloride (5 ml)
4. extractionextracted with ethyl acetate (2×10 ml)
5. customThe combined organics are purified by flash chromatography