Diisopropylamine → HCID 15617524, compound

Temperature

0 °C

Diisopropylamine (61.8 ml, 441 mmoles) was dissolved in tetrahydrofuran (200 ml) and cooled to 0° C. in an ice-methanol bath while stirring under argon. A 2.6 M solution of n-butyllithium in hexane (170 ml, 441 mmoles) was added dropwise. Toluic acid (30.0 g, 221 mmoles) was then added and the reaction immediately turned a deep red color. This mixture was added slowly to a solution of 1,6-dibromohexane (84 ml, 551 mmoles) in tetrahydrofuran (200 ml) at 0° C. Following the addition, the ice bath was removed and the reaction mixture was stirred at room temperature under argon for 18 hours. The solvent was evaporated and the residue dissolved in ether. The ether was extracted with cold 1 N sodium hydroxide solution. The pH of the aqueous phase was adjusted to 8.0 with cold concentrated hydrochloric acid and extracted with ether. The ether extract was dried over anhydrous magnesium sulfate, filtered and evaporated to afford the desired product.

1. customthe reaction
2. additionthe addition
3. customthe ice bath was removed
4. stirringthe reaction mixture was stirred at room temperature under argon for 18 hours
5. customThe solvent was evaporated
6. dissolutionthe residue dissolved in ether
7. extractionThe ether was extracted with cold 1 N sodium hydroxide solution
8. extractionextracted with ether
9. extractionThe ether extract
10. dry with materialwas dried over anhydrous magnesium sulfate
11. filtrationfiltered
12. customevaporated

ORD record

ord-89f438f0e7fc4e5e8b79048ae0a54d74

Source dataset

uspto-grants-1988_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04730005