Lithium Hexamethyldisilazide → Methyl 4-[2-(2-benzyloxy-3-pyridyl)ethenyl]benzoate

Participants

Reaction Steps

(4-Methoxycarbonylbenzyl)triphenylphosphonium bromide (16.6 g, 33.8 mmol) was suspended in THF (70 ml) under Argon. Lithium bis(trimethylsilyl)amide (1M in THF, 40.5 ml) was added. The reaction mixture was stirred for 1 hour at ambient temperature; the colour changed to orange. 2-Benzyloxy-3-pyridinecarbaldehyde (7.2 g, 33.8 mmol) was added as a solution in THF (50 ml) and the reaction mixture was stirred at amibent temperature overnight (shielded from light). The reaction mixture was partitioned between EtOAc/water, the organic phase was dried (MgSO4) and evaporated. Purification by chromatography (SiO2, eluting with CH2Cl2 /hexane) gave methyl 4-[2-(2-benzyloxy-3-pyridyl)ethenyl]benzoate (9.2 g, 79%).

Provenance & Evidence