Reaktion #1569631

Reaktionsgleichung

methyl 4-(bromomethyl)benzoate

lithium diisopropylamide

4-(3-chlorophenyl)-2,3-dihydro-1H-inden-1-one

→

methyl 4-((4-(3-chlorophenyl)-1-oxo-2,3-dihydro-1H-inden-2-yl)methyl)benzoate

Ausbeute 5.3%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITAfter 1 h at −78° C.
2. 2
   workup.WAITAfter 1 h at 0° C.
3. 3
   Sonstigethe reaction was quenched with saturated aqueous NH4Cl (50 mL)
4. 4
   Extraktionextracted with EtOAc (3×50 mL)
5. 5
   TrocknenThe combined organic extracts were dried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe resulting crude residue was purified by combiflash (40 g column, hexanes→30% EtOAc/hexanes, gradient)

Vorschrift

A solution of lithium diisopropylamide (2.0 M in THF, 0.49 mL, 0.98 mmol) was added to a solution of 4-(3-chlorophenyl)-2,3-dihydro-1H-inden-1-one (235 mg, 0.97 mmol) in THF (3.3 mL) at −78° C. After 1 h at −78° C., a solution of methyl 4-(bromomethyl)benzoate (229 mg, 1.0 mmol) in THF (1.7 mL) was added via cannula. After 1 h at −78° C., the mixture was allowed to slowly warm to 0° C. After 1 h at 0° C., the reaction was quenched with saturated aqueous NH4Cl (50 mL) and extracted with EtOAc (3×50 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The resulting crude residue was purified by combiflash (40 g column, hexanes→30% EtOAc/hexanes, gradient) to afford 20 mg (5%) of methyl 4-((4-(3-chlorophenyl)-1-oxo-2,3-dihydro-1H-inden-2-yl)methyl)benzoate.

Quelle