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US 5,349,071 AGranted
Process for preparing tertiary alkynols
AssigneeLoyola University of Chicago
InventorJames H. Babler
Life of this patent
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Abstract
Processes for synthesizing tertiary alkynols by reacting carbonyl-group-containing compounds with alkynes in the presence of a basic catalyst are disclosed. Preferred products are 6,10,14-trimethyl-4-pentadecyn-6-ol compounds having the structure: ##STR1## A preferred, novel compound, 6,10,14-trimethyl-4-pentadecyne-2,6-diol, can be used in the synthesis of Vitamin E or Vitamin K.sub.1.
Claims33
A process for synthesizing a tertiary alkynol comprising:
- a) forming a reaction mixture in a non-hydroxylic organic solvent containing:
- i) a carbonyl-group-containing compound of the formula RCH.sub.2 COCH.sub.2 R.sup.1 ;
- ii) an alkyne having the formula R.sup.11 C.dbd.CH;
- and
- iii) a catalytic amount of a base stronger than an alkali-metal carbonate;
- wherein R and R.sup.1 are alkyl or H or form part of an alicyclic ring;
- and R.sup.11 is an alkyl, alkenyl, alkoxyalkyl, hydroxyalkyl or the alkali-metal salt thereof, aryl or arylalkyl group, provided that when either R or R.sup.1 is H, said carbonyl-group-containing compound is slowly added to said reaction mixture, and when R or R.sup.11 contains a carbon-carbon double bond, the double bond is not conjugated with the carbonyl group of said carbonyl-group containing compound;
- and
- b) maintaining said reaction mixture until said tertiary alkynol is formed.
6 more elements
Dependencies are inferred from the claim text.