Acetic Acid → HCID 14699194, compound

Participants

Reaction Steps

To a stirred solution of diisopropylamine (3.13 ml, 22.38 mmoles) in 80 ml of anhydrous THF at -78° C., under nitrogen, was added 8.24 ml (20.59 mmoles) of a 2.5M hexane solution of n-butyllithium. After stirring for 5 minutes, a solution of methyl acetoacetate (1.07 g, 9.19 mmoles) in 10 ml of THF was added dropwise over 15 minutes. The dry ice acetone bath was removed and, after 10 minutes, an ice bath was applied. The mixture was stirred for 1.5 hours. To this mixture was added a solution of (E)-3-[7,9-di-(4-fluorophenyl)spiro[4.5]deca-6,8-dien-6-yl]2-propenaldehyde (2.7 g, 7.17 mmoles) in 50 ml of THF dropwise over 40 minutes. The mixture was stirred in ice for 1 hour and a solution of glacial acetic acid (2.46 ml, 42.97 mmoles) in 10 ml of THF was added dropwise over 5 minutes. The mixture was poured into 250 ml of ethylacetate and was extracted with water, sodium bicarbonate and brine. The organic layer was dried over magnesium sulfate and was evaporated in vacuo to give 3.3 g of product having an m.p. of 96-9° C.

Provenance & Evidence