Reacción #69413

Ecuación de reacción

lithium diisopropylamide

3-Isobutoxycyclopent-2-enone

1-bromo-4-(bromomethyl)benzene

→

5

Rendimiento 40.0%

5-(4-Bromobenzyl)-3-isobutoxycyclopent-2-enone

Rendimiento 40.0%

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe resulting mixture was stirred for 1 h
2. 2
   Otroto rise to rt
3. 3
   OtroThe reaction was quenched with a saturated aqueous solution of ammonium chloride (3.0 mL)
4. 4
   ExtracciónThe aqueous phase was extracted with ethyl acetate (2×10 mL)
5. 5
   Lavadowere washed with brine
6. 6
   Secadodried over magnesium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated in vacuo
9. 9
   OtroPurification by silica gel column chromatography

Procedimiento

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).

Fuente