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US 6,596,879 B2Granted
Process for the synthesis of 1,3-diols
AssigneeWarner-Lambert Company
InventorsRobert Lee Bosch, Richard Joseph McCabe, Thomas Norman Nanninga, Robert Joseph Stahl
Life of this patent
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Abstract
An improved process for the preparation of cis-1,3-diols is described where a beta hydroxy ketone is treated with a trialkylborane or dialkylalkoxyborane or a mixture of a trialkylborane and a dialkylalkoxyborane followed by recovery and reuse of the alkylborane species to convert additional beta hydroxy ketone to the cis-1,3-diol.
Claims16
A process for the preparation of a compound of Formula I
- wherein R is,
- which comprises:
- Step (a) treating a compound of Formula II
- wherein R and R1 are as defined above with a trialkylborane or dialkylalkoxyborane or a mixture of a trialkylborane and a dialkylalkoxyborane in a solvent;
- Step (b) adding an alkali metal hydride at about −110° C. to about −50° C.;
- Step (c) concentrating the reaction by distillation to afford a compound of Formula I and a distillate containing alkylborane species;
- and
- Step (d) treating additional compound of Formula II or III with the distillate from Step (c) containing recovered alkylborane species, and repeating Steps (b) and (c) as desired to afford additional compound of Formula I.
5 more elements
A process for the preparation of a compound of Formula I
- wherein R is,
- which comprises:
- Step (a) treating a compound of Formula II
- wherein R and R1 are as defined above with a synergistic combination of a trialkylborane and a dialkylalkoxyborane in a solvent;
- and Step (b) adding an alkali metal hydride at about −110° C. to about −50° C. to afford a compound of Formula I.
2 more elements
Dependencies are inferred from the claim text.