3-(2-methylpropoxy)cyclopent-2-en-1-one

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Isobutoxycyclopent-2-enone (3, 0.130 g, 0.84 mmol) in anhydrous tetrahydrofuran (2.0 mL) was cooled to −78° C. and a freshly prepared 1M solution of lithium diisopropylamide (1.0 mL, 1.0 mmol) was added dropwise. The mixture was stirred at −78° C. for 45 min and a solution of 1-bromo-4-(bromomethyl)benzene (0.210 g, 0.84 mmol) in anhydrous tetrahydrofuran (3.0 mL) was added dropwise. The resulting mixture was stirred for 1 h allowing the temperature to rise to rt. The reaction was quenched with a saturated aqueous solution of ammonium chloride (3.0 mL). The aqueous phase was extracted with ethyl acetate (2×10 mL) and combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by silica gel column chromatography using a gradient of ethyl acetate in hexanes as eluant provided 5 as a white solid (40% yield). The resulting mixture was stirred for 1 h to rise to rt The reaction was quenched with a saturated aqueous solution of ammonium chloride (3.0 mL) The aqueous phase was extracted with ethyl acetate (2×10 mL) were washed with brine dried over magnesium sulfate filtered concentrated in vacuo Purification by silica gel column chromatography

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Isobutoxycyclopent-2-enone (3, 0.130 g, 0.84 mmol) in anhydrous tetrahydrofuran (2.0 mL) was cooled to −78° C. and a freshly prepared 1M solution of lithium diisopropylamide (1.0 mL, 1.0 mmol) was added dropwise. The mixture was stirred at −78° C. for 45 min and a solution of 1-bromo-4-(bromomethyl)benzene (0.210 g, 0.84 mmol) in anhydrous tetrahydrofuran (3.0 mL) was added dropwise. The resulting mixture was stirred for 1 h allowing the temperature to rise to rt. The reaction was quenched with a saturated aqueous solution of ammonium chloride (3.0 mL). The aqueous phase was extracted with ethyl acetate (2×10 mL) and combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by silica gel column chromatography using a gradient of ethyl acetate in hexanes as eluant provided 5 as a white solid (40% yield). The resulting mixture was stirred for 1 h to rise to rt The reaction was quenched with a saturated aqueous solution of ammonium chloride (3.0 mL) The aqueous phase was extracted with ethyl acetate (2×10 mL) were washed with brine dried over magnesium sulfate filtered concentrated in vacuo Purification by silica gel column chromatography

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Isobutoxycyclopent-2-enone (3, 0.130 g, 0.84 mmol) in anhydrous tetrahydrofuran (2.0 mL) was cooled to −78° C. and a freshly prepared 1M solution of lithium diisopropylamide (1.0 mL, 1.0 mmol) was added dropwise. The mixture was stirred at −78° C. for 45 min and a solution of 1-bromo-4-(bromomethyl)benzene (0.210 g, 0.84 mmol) in anhydrous tetrahydrofuran (3.0 mL) was added dropwise. The resulting mixture was stirred for 1 h allowing the temperature to rise to rt. The reaction was quenched with a saturated aqueous solution of ammonium chloride (3.0 mL). The aqueous phase was extracted with ethyl acetate (2×10 mL) and combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by silica gel column chromatography using a gradient of ethyl acetate in hexanes as eluant provided 5 as a white solid (40% yield). The resulting mixture was stirred for 1 h to rise to rt The reaction was quenched with a saturated aqueous solution of ammonium chloride (3.0 mL) The aqueous phase was extracted with ethyl acetate (2×10 mL) were washed with brine dried over magnesium sulfate filtered concentrated in vacuo Purification by silica gel column chromatography