Potassium bis(trimethylsilyl)amide → HCID 67106787, compound

Participants

Reaction Conditions

Reaction Steps

0.5N KHMDS (1.81 ml, 0.90 mmol) was added to a solution of triethyl phosphonoacetate (0.20 g, 0.90 mmol) in tetrahydrofuran (5 ml) at −78° C. The solution was stirred at −78° C. for 15 minutes, then a suspension of 5-formyl-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide (may be prepared as described in Example 66; 200 mg, 0.60 mmol) in tetrahydrofuran (10 ml) was added dropwise over 3 minutes. The mixture was stirred at −78° C. for 15 minutes. It was then allowed to warm to room temperature and stirred for a further hour. The reaction was quenched with saturated NH4Cl (10 ml) and extracted with ethyl acetate (2×10 ml). The combined organic layers were dried (MgSO4) and the solvent removed in vacuo to give a brown solid. Trituration with 2:1 ethyl acetate/hexane yielded the title compound as a brown solid. 160 mg.

Provenance & Evidence