Ethyl Acetoacetate → Ethyl 9,9-bis(4-fluorophenyl)-5-hydroxy-8-(1-ethyl-1H-tetrazol-5-yl)-3-oxo-6,8-nonadienoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.5 g (1.4 mmoles) of 5,5-bis(4-fluorophenyl)-4-(1-ethyl-1H-tetrazol-5-yl)2,4-pentadienal in tetrahydrofuran at -50° C., was added 1.75 mL of 0.8M (1.4 mmoles) of a freshly prepared solution of ethyl acetoacetate dianion [described in Example 10]. The solution was stirred for 30 minutes at -50° C. and then allowed to warm to -10° C. during the next 30 minutes. The solution was quenched with 1N HCl and extracted with methylene chloride. The organic extracts were dried and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with chloroform to give 0.4 g of the title compound as an oil. MS (CI): m/e=497 for (M+H)+.

Provenance & Evidence