Diisopropylamine → 5-(7-Bromoheptyl)-3-methylisoxazole

Temperature

-70 °C

To a solution of diisopropylamine (8.4 ml, 0.06 mol) in THF, was added, at -5° C., and under nitrogen, n-butyllithium (1.6M in Hexane, 37.5 ml, 0.06 mole). After the addition was complete, the solution was cooled to -70° C. and 3,5-dimethylisoxazole (5.82 g, 0.06 mol) in THF (20 ml) was added dropwise. The mixture was stirred for an additional hour at -70° C., then added, via nitrogen purge, to a solution of 1,6-dibromohexane (58.56 g, 0.24 mol) in THF (40 ml), and chilled to -70° C. with stirring. The mixture was allowed to gradually warm to room temperature and then stirred overnight. After quenching with saturated solution of ammonium chloride (30 ml), the mixture was extracted with isopropylacetate (250 ml) and the extract was washed with distilled water and dried. Removal of the solvent and excess 1,6-dibromohexane gave an oil which was purified by c.c. (EtAcO/Hexane; 1:4).

1. additionAfter the addition
2. additionadded, via nitrogen
3. temperaturechilled to -70° C.
4. stirringwith stirring
5. temperatureto gradually warm to room temperature
6. stirringstirred overnight
7. customAfter quenching with saturated solution of ammonium chloride (30 ml)
8. extractionthe mixture was extracted with isopropylacetate (250 ml)
9. washthe extract was washed with distilled water
10. customdried
11. customRemoval of the solvent and excess 1,6-dibromohexane
12. customgave an oil which
13. customwas purified by c.c

ORD record

ord-c7a55eb3f47641eb9186fc4fa78c2335

Source dataset

uspto-grants-1991_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05026848