4-Bromoanisole → 1-(4-Methoxyphenyl)-3-phenylindane-2-carboxylic acid

Ethyl (1RS)[1-Hydroxy-1-(4-methoxyphenyl)]-3-phenylindene-2-carboxylate. To dry magnesium turnings (0.88 g, 36 mmol) under an argon atmosphere was added, portionwise, a solution of p-bromoanisole (4.5 ml, 36 mmol) in 5% THF/Et2O (37 ml). The resulting p-methoxyphenyl magnesium bromide solution was added to a solution of ethyl 1-oxo-3-phenylindene-2-carboxylate (5.0 g, 18 mmol) in Et2O (300 ml) under an argon atmosphere at 0° C. The resulting mixture was allowed to warm to room temperature and was stirred for 10 min. The mixture was partitioned between 3M HCl (100 ml) and EtOAc (200 ml). The organic extract was washed successively with H2O, aqueous NaHCO3, H2O and saturated aqueous NaCl and dried (Na2 SO4). The solvent was removed in vacuo to provide a yellow oil which was treated with Et2O/hexanes. The solid which formed was collected by filtration (3.47 g). The filtrate was concentrated under reduced pressure and purified by flash chromatography. The material which was isolated was treated with Et2O/hexanes, and the additional solid which formed (1.76 g, 75% total yield) was collected by filtration to afford the title compound.

1. customThe mixture was partitioned between 3M HCl (100 ml) and EtOAc (200 ml)
2. extractionThe organic extract
3. washwas washed successively with H2O, aqueous NaHCO3, H2O and saturated aqueous NaCl
4. customdried (Na2 SO4)
5. customThe solvent was removed in vacuo
6. customto provide a yellow oil which
7. customThe solid which formed
8. filtrationwas collected by filtration (3.47 g)
9. concentrationThe filtrate was concentrated under reduced pressure
10. custompurified by flash chromatography
11. customThe material which was isolated
12. customthe additional solid which formed
13. custom(1.76 g, 75% total yield)
14. filtrationwas collected by filtration

ORD-Eintrag

ord-e011751a355944b0893609e4feba00e1

Quelldatensatz

uspto-grants-1998_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05716984