Sodium Chloride → HCID 550341, compound

Temperature

0 °C

A solution of 101.2 g of diisopropylamine in 125 ml of absolute tetrahydrofuran was combined under argon at -20° C. dropwise with 610 ml of a 1.64N butyllithium solution in hexane. The temperature was allowed to rise for a short time to about 0° C. and then, at -50° to -60° C., 116 g of ethyl isobutyrate was added dropwise to the lithium diisopropylamide solution. The reaction solution was stirred for one hour at 0° C., then cooled to -40° C. and thereafter added to a solution of 200 g of 4-bromo-2-methyl-2-butene (dimethylallyl bromide) in 60 ml of absolute dimethyl sulfoxide, maintained at -20° C. While allowing the temperature to rise to room temperature, the reaction mixture was agitated for 60 hours and then combined with 250 ml of saturated sodium chloride solution. The organic phase was separated, and the aqueous phase was extracted five times with respectively 200 ml of a 1/1 mixture of ether and hexane. The combined organic phases were washed neutral with 0.5N hydrochloric acid and saturated sodium chloride solution, dried over magnesium sulfate, and concentrated on a forced circulation evaporator. The residue was distilled under vacuum, thus obtaining 91.5 g of the desired ester, bp13 76°-81° C.

1. customto rise for a short time to about 0° C.
2. temperaturecooled to -40° C.
3. temperaturemaintained at -20° C
4. customto rise to room temperature
5. stirringthe reaction mixture was agitated for 60 hours
6. customThe organic phase was separated
7. extractionthe aqueous phase was extracted five times
8. additionwith respectively 200 ml of a 1/1 mixture of ether and hexane
9. washThe combined organic phases were washed neutral with 0.5N hydrochloric acid and saturated sodium chloride solution
10. dry with materialdried over magnesium sulfate
11. concentrationconcentrated on a forced circulation evaporator
12. distillationThe residue was distilled under vacuum

ORD record

ord-d631b19453eb4359882b057a4f749615

Source dataset

uspto-grants-1986_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04567195