135705-63-4Relevant articles and documents
Reaction of ethyl acetoacetate with steroidal enones: Synthesis of steroidal pyrans and related compounds
Ahmad, M S,Ebbar, Fakhri El
, p. 658 - 661 (2007/10/02)
Reaction of ethyl acetoacetate with several steroidal enones in the cholestane series, in the presence of fused zinc chloride in acetic acid-acetic anhydride, has been described.Cholesta-3,5-dien-7-one (I) furnishes 7-oxo-3-(1'carbethoxypropan-2'-one)-cholest-5-ene (VII) and 7-acetoxy-3'-carbethoxy-2'-methylcholest-6-eno-3,4-dihydropyran (VIII).Under similar reaction conditions II and III provide the dienone (I), VII and VIII.Cholest-5-en-7-one (IV) affords 7-acetoxy-5ξ-(1'-propan-2'-one)-cholest 7-ene (IX) and 7-acetoxy-5ξ-(1'-carbethoxypropan-2'-one)-cholest-6-ene (X).Cholest-4-en-3-one (V) likewise gives 5α-acetoxycholestan-3-one (XI) and the pyrans, 3-acetoxy-3'-carbethoxy-2'-methylcholestanol-3',4'-dihydropyran (XII) and its 3-hydroxy analogue (XIII).Out of curosity the reaction of 3α,5α-cyclo-cholestan-6-one with ethyl acetoacetate has also been carried out.This provides 3β-acetoxy-5α-cholestan-6-one (XIV), cholest-4-en-6-one (XV) and the latter's artefact, 3'-carbethoxy-2'-methyl-4,6-cholestadieno2',3'-dihydropyran (XVI).The structures of the compounds have been established by elemental analyses, spectral data and in some cases by comparison with the known samples.