Dimethylformamide → 3-(1-(tert-Butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-fluorobenzaldehyde

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Reaction Conditions

Reaction Steps

sec-Butyllithium (1.4M in cyclohexane, 3.54 mL) was added to dry tetrahydrofuran (10 mL) under nitrogen and the solution cooled to −78° C. N1-(2-(dimethylamino)ethyl)-N1,N2,N2-trimethylethane-1,2-diamine (0.859 g) was added slowly dropwise. A solution of tert-butyl(2-(2-fluorophenyl)-2-methylpropoxy)dimethylsilane (example 90, step e) (1.4 g) in dry tetrahydrofuran (3 mL) was then added dropwise over 5 minutes. The reaction mixture was stirred for 2 hours at −78° C. DMF (2.69 mL) was added dropwise over 5 minutes and the mixture stirred at −78° C. for 1 hour followed by room temperature for 45 minutes. The reaction mixture was quenched by addition of water. Ethyl acetate (200 mL) was added and the organic washed three times with water followed by twice with 2M HCl and twice with water, then brine and dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure. The crude product was purified by flash silica chromatography, elution gradient 1 to 5% ethyl acetate in isohexane. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 0.98 g.

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