Acetone → HCID 53921069, compound

Participants

Reaction Steps

3-(4'-fluorophenyl)-1-hyroxy-6-methyl-1-pyrid-4-ylindane (12.0 g) was refluxed with ethyl bromoacetate (7.5 g) in acetone (100 ml) for 4 hrs. The reaction mixture was cooled in a refrigerator over night and the precipitate filtered off. Yield: 16.8 g (91.9%) of the pyridiniumbromide. MP: 196°-198° C. (dec.). The bromide (15.0 g) was dissolved in methanol (150 ml), and ice cooled, NaBH4 (5.0 g) was added during a period of 1 h. The reaction mixture was finally stirred for another 1/2 h at room temperature and subsequently poured into NH4Cl (25 g) in 1 L of H2O. The H2O phase was extracted with ethyl acetate (2×200 ml), the combined organic phases dried (MgSO4) and the solvent evaporated yielding 11.7 g (92.7%) of 1-(1-ethylcarboxymethyl-1,2,3,6-tetrahydropyrid-4-yl)-3-(4'-fluorphenyl)-1-hydroxy-6-methylindane. MP: 119° -20° C.

Provenance & Evidence