C - Chemistry – Metallurgy – 07 – C
Patent
C - Chemistry, Metallurgy
07
C
260/325.5, 260/5
C07C 235/18 (2006.01) C07C 45/51 (2006.01) C07C 49/252 (2006.01) C07C 221/00 (2006.01) C07C 225/16 (2006.01) C07D 295/104 (2006.01)
Patent
CA 2023373
HYDROXYLATED ENE KETONES, ACETYLENIC GRIGNARDS AND HYDROXYLATED YNE KETONES THEREFROM Abstract An alpha-hydroxyl-alpha,alpha-di(inert-substituted)- gamma',delta'-yne ketone can be prepared by a procedure comprising contacting an acetylenic Grignard reagent with an alpha-hydroxyl-alpha,alpha-di(inert substituted)- alpha',beta'-ene ketone, and the alpha-hydroxyl-alpha,alpha- di(inert-substituted)-alpha',beta'-ene ketone can be prepared by a procedure comprising steps of contacting, first, an alkoxy allene with a lithium donating organic agent, second, product of the first step with a di(inert-substituted)ketone, and third, product of the second step with an acidic substance. For example. 1-cyclobutyl-7-(N,N-dimethylamino)-1-hydroxy-1-phenylhept- 5-yn-2-one, hydrochloride salt (ML-1012), can be prepared by the reaction of 1-cyclobutyl-1-hydroxy-1-phenylbut-3-en- 2-one and 1-(N,N-dimethylamino)-2-propyn-3-magnesium chloride, followed by salt formation with hydrogen chloride gas, and the 1-cyclobutyl-1-hydroxy-1-phenylbut-3-en-2-one can be prepared by the serial reactions of (1) 1-methoxy allene with n-butyllithium, (2) product of this first step with cyclobutylphenyl ketone, and (3) product of this second step with sulfuric acid. MLI-81/CJR
Barf Gerrit Andre
Borcherding David Roger
Hoeve Wolten Ten
Koek Johannes Nicolaas
Wynberg Hans
Marion Merrell Dow Inc.
Osler Hoskin & Harcourt Llp
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