Dimethylformamide → 3-[2-(Tetrahydropyran-2-yloxy)-ethyl]-benzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-[2-(3-bromo-phenyl)-ethoxy]-tetrahydro-pyran (20 g) in anhydrous tetrahydrofuran (300 mL) at −78° C. was added n-butyl lithium (2.5M in hexanes, 33.6 ml) dropwise over 5 minutes. The dark solution was kept at −78° C. for 30 minutes then N,N-dimethylformamide (16.35 ml) was added. The mixture was stirred −78° C. for half hour then quenched with aqueous ammonium acetate, and allowed to warm to room temperature. The resulting mixture was extracted with ethyl acetate, and the organics washed with brine, dried over sodium sulfate and concentrated in vacuo to give a yellow/orange oil (16.0 g). The material was used in the next step without further purification.

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