Tetrahydrofuran → (E)-3-{8-(4-fluoro-3-methylphenyl)-10,10-dimethyl-1,5dithiaspiro{5.5}undec-8-en-9-yl}propenal

Participants

Reaction Conditions

Reaction Steps

To a -20° C. solution of LDA (19.0 mmol) in 60 mL anhydrous THF was added ethylidenecyclohexylamine (Org. Syn. 50, 66) (2.38 gm, 19.0 mmol). The solution was stirred for 30 min, cooled to -78° C. and a solution of 8 (3.50 g, 10.0 mmol) in 60 mL was added. The mixture was stirred for 3 h, diluted with ether and quenched with H2O. The organic layer was washed with H2O and brine and dried (MgSO4). Removal of the volatiles in vacuo and purification of the residue by HPLC using 10:1 hexanes:EtOAc provided 1.6 g of the orange color gum.

Provenance & Evidence