C - Chemistry – Metallurgy – 07 – F
Patent
C - Chemistry, Metallurgy
07
F
C07F 7/12 (2006.01) C07B 37/02 (2006.01) C07C 45/69 (2006.01) C07C 49/303 (2006.01) C07C 49/76 (2006.01) C07D 319/08 (2006.01) C07F 7/18 (2006.01) C07J 1/00 (2006.01)
Patent
CA 2172816
This invention describes an alkylating agent that contains an aluminum reagent Alk3-m AlLm, in which Alk means a methyl, ethyl, n- or i-propyl, n-, i- or tert-butyl, pentyl, hexyl, heptyl or octyl group, which all can also be branched, L means an ethoxy group, a chlorine or bromine atom, and m is equal to 1 or 2, as an alkyl source or else zinc dimethyl as a methyl source, which contains in addition catalytic amounts of one or more copper(I) and/or copper(II) compounds and one (or more) silyl reagent(s) of general formula III R1R2R3SiZ (III), in which R1, R2 and R3 can be the same or different and mean a straight-chain or branched-chain alkyl radical with 1 carbon atom, or in the branched-chain case, with 3 to 10 carbon atoms, an alkyl radical optionally substituted with 1 to 3 chlorine atoms or 1 to 3 straight-chain or branched-chain alkoxy or alkyl radicals with 1 carbon atom or, in the branched-chain case, 3 to 6 carbon atoms, and Z means a chlorine, bromine or iodine atom, the cyano radical, a perfluoroalkylsulfonyloxy radical [(CnF2n+1SO2O-), with n = 1, 2, 3 or 4], the mesylate radical CH3SO2O-, the tosyl radical p-CH3-C6H4-SO2O- or another leaving group, as well as a process for 1,4-addition of an alkyl group to an .alpha.,.beta.-unsaturated ketone or an .alpha.,.beta.-double unsaturated ketone or to an .alpha.,.beta.-unsaturated aldehyde with use of the agent according to the invention. The alkylating agent yields biologically active compounds in excellent yields and the new alkylating agent/ process is distinguished by its environmental compatibility based on a CKW (chlorinated hydrocarbon)-free reaction medium.
Nickisch Klaus
Westermann Jurgen
Bereskin & Parr Llp/s.e.n.c.r.l.,s.r.l.
Schering Aktiengesellschaft
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