4-Bromoanisole → Ethyl(1RS)-1-Hydroxy-1-(4-methoxyphenyl)-3-(3,4-methylenedioxyphenyl)indene-2-carboxylate

A solution of 4-bromoanisole (0.89 g, 5.0 mmol) in 9:1 Et2O/THF (10 ml) was added to magnesium turnings (0.105 g, 5.0 mmol), and the resulting mixture was allowed to stir for 30 min. The resultant 4-methoxyphenyl magnesium bromide was added dropwise to a solution of ethyl 3-(3,4-methylenedioxyphenyl)-1-oxoindene-2-carboxylate (0.77 g, 2.4 mmol) in 10:1 Et2O/THF (55 ml) at 0° C. The resulting mixture was stirred at 0° C. for 1 h and was then partitioned between EtOAc and 1M HCl. The aqueous phase was extracted with EtOAc, and the combined organic extracts were washed successively with 5% aqueous NaHCO3 and saturated aqueous NaCl and dried (MgSO4). The solvent was removed under reduced pressure, and the residue was purified by flash chromatography on silica gel, eluting with 10% EtOAc/hexanes to afford the title compound as a yellow glassy solid (0.80 g, 80%).

1. stirringThe resulting mixture was stirred at 0° C. for 1 h
2. customwas then partitioned between EtOAc and 1M HCl
3. extractionThe aqueous phase was extracted with EtOAc
4. washthe combined organic extracts were washed successively with 5% aqueous NaHCO3 and saturated aqueous NaCl
5. dry with materialdried (MgSO4)
6. customThe solvent was removed under reduced pressure
7. customthe residue was purified by flash chromatography on silica gel
8. washeluting with 10% EtOAc/hexanes

ORD-Eintrag

ord-390a0df80572477b81bfbb7effca0647

Quelldatensatz

uspto-grants-1998_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05817693