Diisopropylamine → HCID 66760696, compound

Temperature

-78 °C

To a solution of diisopropylamine (1.1 eq.) in THF (0.12 M) was added, at −78° C., n-butyllithium (1.6 M hexane solution, 1.1 eq.) over a period of 5 min. The resulting mixture was stirred at −78° C. for 15 min and then warmed at RT for 10 min. With the reaction mixture re-cooled to −78° C., ethyl pent-4-enoate (1.1 eq.) was added dropwise as a 1.6 M THF solution. The resulting solution was stirred for 30 min at −78° C. Finally, tert-butyl{2-[4-(iodomethyl)phenoxy]ethoxy}dimethylsilane (1 eq.) was added dropwise as a 1.5 M THF solution. The reaction mixture was allowed to warm slowly to RT over 12 h. After the reaction was carefully quenched with the addition of a sat. aq. NH4Cl solution, the reaction mixture was extracted with ether. The combined organic extracts were washed with brine, dried over MgSO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of column chromatography (SiO2, 10:1 (v/v) Hex:ether) afforded the title compound as a colorless oil.

1. temperaturewarmed at RT for 10 min
2. temperatureWith the reaction mixture re-cooled to −78° C.
3. stirringThe resulting solution was stirred for 30 min at −78° C
4. temperatureto warm slowly to RT over 12 h
5. customAfter the reaction was carefully quenched with the addition of a sat. aq. NH4Cl solution
6. extractionthe reaction mixture was extracted with ether
7. washThe combined organic extracts were washed with brine
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationthe filtrate concentrated in vacuo
11. customPurification of the crude product
12. customthus obtained by way of column chromatography (SiO2, 10:1 (v/v) Hex:ether)

ORD record

ord-8d2a7e042dc644bbac90caa3297f36dd

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063105B2