반응 #1569632

반응 방정식

methyl 4-(bromomethyl)benzoate

lithium diisopropylamide

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

→

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

수율 13.3%

용매

THF

THF

반응 조건

후처리

1. 1
   workup.WAITAfter 1 h at −78° C.
2. 2
   workup.WAITAfter 30 min at 0° C.
3. 3
   기타the reaction was quenched with saturated aqueous NH4Cl (25 mL)
4. 4
   workup.ADDITIONdiluted with water (10 mL)
5. 5
   추출extracted with EtOAc (3×50 mL)
6. 6
   건조The combined organic extracts were dried (Na2SO4)
7. 7
   여과filtered
8. 8
   농축concentrated
9. 9
   기타The resulting crude residue was purified by combiflash (40 g column, hexanes→30% EtOAc/hexanes, gradient)

실험 절차

A solution of lithium diisopropylamide (2.0 M in THF, 0.50 mL, 1.0 mmol) was added to a solution of 4-(naphthalen-1-yl)-2,3-dihydro-1H-inden-1-one (254 mg, 0.98 mmol) in THF (3.4 mL) at −78° C. After 1 h at −78° C., a solution of methyl 4-(bromomethyl)benzoate (230 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 30 min at 0° C., the reaction was quenched with saturated aqueous NH4Cl (25 mL), diluted with water (10 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 53 mg (13%) of methyl 4-((4-(naphthalen-1-yl)-1-oxo-2,3-dihydro-1H-inden-2-yl)methyl)benzoate.

출처