Ethyl Acetoacetate → HCID 131711958, compound

Participants

Reaction Conditions

Reaction Steps

8-t-Butyldiphenylsiloxy-3,7-dimethyl-1-octen-3-ol (60.33 g) is treated with ethyl acetoacetate (28.8 ml) and anhydrous sodium acetate (232 mg) and the mixture is allowed to stir for 2 hours at 205° C. under a short path distillation head to remove the ethanol formed in the reaction. The crude reaction mixture is purified via silica gel chromatography using ethyl acetate-hexane gradients to give 6 E/Z-1-t-butyldiphenylsiloxy-2,6-dimethyl-10-oxo-undec-6 -ene (32.9 g, 50%) as a yellow oil: ir (neat) 5.8μ (C=O); nmr (CDCl3)δ0.9 (d, CH3CH<), 1.05 [s, (CH3)3C], ##STR7## 2.08 ##STR8## 3.48 (d, 2H, OCH2CH<), 5.03 (b, 1H, C=CH--), 7.17-7.8 (m, 10 H, 2φ); m.s., M+ 450 (parent peak) not observed but M-57 (t-Bu) 393 present. A mixture of 60/40 E/Z isomers is observed by gas chromatography.

Provenance & Evidence