Dimethylformamide → 3-(2-(tert-Butyldimethylsilyloxy)ethyl)-2-methylbenzaldehyde

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Reaction Conditions

Reaction Steps

A colourless solution of (3-bromo-2-methylphenethoxy)(tert-butyl)dimethylsilane [Aromatic Intermediate 22, step c] (2.06 g) in THF (40 mL) was cooled to −78° C. under an atmosphere of nitrogen and treated with butyllithium (2.1M in hexanes, 3.3 mL), added dropwise over 3 minutes. The resulting pale yellow solution was stirred at −78° C. for 30 minutes, treated with N,N-dimethylformamide (0.73 mL) added dropwise over 2 minutes to give a colourless solution, stirred at −78° C. for a further 30 minutes, then removed from the cooling bath and allowed to warm to room temperature over 45 minutes. The solution was quenched by the addition of 10% aqueous ammonium chloride (100 mL), and the resulting mixture was extracted twice with diethyl ether. The combined organic phases were washed with brine, dried over anhydrous magnesium sulphate and concentrated in vacuo to afford the titled compound as a pale yellow oil. Yield 1.74 g.

Provenance & Evidence