Ammonium Chloride → 6-[(4-tert-Butylphenyl)(hydroxy)methyl]-5-(4-fluorophenyl)-7-isopropylspiro[chromen-2,1'-cyclo-butan]-4(3H)-one

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Reaction Conditions

Reaction Steps

Under argon, 0.30 g (0.851 mmol) of 5-(4-fluorophenyl)-7-isopropyl-4-oxo-3,4-dihydrospiro-[chromen-2,1′-cyclobutane]-6-carbaldehyde (Example 51A) is suspended in 6 ml of tetrahydrofuran and cooled to −78° C. 2.54 ml (1.28 mmol) of a freshly prepared 0.5 M solution of [4-(tert-butyl)phenyl]magnesium bromide in tetrahydrofuran are added slowly. The mixture is briefly stirred at −78° C. and then warmed to 0° C. After about 1.5 h, saturated ammonium chloride solution is added and the mixture is diluted with a little 1 N hydrochloric acid and extracted repeatedly with ethyl acetate. The combined organic phases are washed twice with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The crude product is purified a little at a time by preparative HPLC (method 12). This gives 0.239 g (58% of theory) of the title compound.

Provenance & Evidence