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US 4,284,827 AGranted
Process to prepare metalated olefins
AssigneeThe Upjohn Company
InventorJerry A. Walker
Life of this patent
Estimating the term…
Abstract
Substituted ethanes (I) are reacted with an alkyl metal reagent to form isomeric metalated olefins (IIIA and IIIB) having a trans (IIIB) to cis (IIIA) ratio of greater than 70:30.
Claims26
A process for the preparation of compounds of the formulas:
- where R.sub.20 is a fluorine or chlorine atom or a --NR.sub..alpha. R.sub..beta. group where R.sub..alpha. and R.sub..beta. are the same or different and are alkyl of 1 thru 3 carbon atoms;
- where X is an oxygen or sulfur atom;
- where Z is alkyl of 1 thru 6 carbon atoms, phenyl or p-methylphenyl where the ratio of trans (IIIB) to cis (IIIA) isomers is greater than 70:30, which comprises reacting a compound of the formula:
- ##STR9## where Q is a chlorine, bromine or iodine or iodine atom or a trimethylamino group with at least 1.5 equivalents of a compound of the formula R-Metal where R is alkyl of 1 thru 5 carbon atoms or phenyl;
- where metal is lithium, sodium, or potassium, in a dry organic solvent in a temperature range of -15.degree. to -120.degree..
2 more elements
A process for the preparation of compounds of the formulas:
- ##STR10## where the ratio of trans (IIIb) to cis (IIIa) isomers is greater than 70:30 which comprises reacting a compound of the formula:
- ##STR11## with 1.5-2 equivalents of n-butyl lithium in a dry organic solvent in a temperature range of -45.degree. to -90.degree..
A process to prepare compounds of the formulas:
- ##STR14## where the ratio of trans (IIb) to cis (IIa) isomers is greater than 70:30 which comprises reacting a compound of the formula ##STR15## with greater than 2 equivalents of n-butyl lithium in a dry organic solvent in a temperature range of -30.degree. to -90.degree. and then quenching with water.
Dependencies are inferred from the claim text.