N,N,N',N'-Tetramethylethylenediamine → 2-Chloro-6-(dimethyl-2-propenylsilyl)-n-ethylbenzamide

Temperatur

-78 °C

A solution of 1.3M s-BuLi in cyclohexane (10.5 mL, 13.6 mmol) was added dropwise to a dry-ice/acetone cooled solution of TMEDA (1.0 mL, 6.5 mmol) in THF (10 mL), followed by the dropwise addition of a solution of the compound of example f (1.0 g, 5.45 mmol) in THF (10 mL). The reaction mixture was stirred at −78° C. for 30 min, then allyldimethylchlorosilane (10.9 mmol) was added and the mixture was stirred for 2.5 h at −78° C. The resulting reaction was warmed to −30° C., quenched with dilute aq citric acid, diluted with water, and extracted with EtOAc (2×). The combined organic extracts were dried (MgSO4), concentrated, and purified by HPLC with 1:19 EtOAc/cyclohexane to give the desired compound as a white solid. m.p. 61-63° C.

1. stirringthe mixture was stirred for 2.5 h at −78° C
2. customThe resulting reaction
3. temperaturewas warmed to −30° C.
4. customquenched with dilute aq citric acid
5. additiondiluted with water
6. extractionextracted with EtOAc (2×)
7. dry with materialThe combined organic extracts were dried (MgSO4)
8. concentrationconcentrated
9. custompurified by HPLC with 1:19 EtOAc/cyclohexane

ORD-Eintrag

ord-ce3f1634a3124e5192a42cde9b57080d

Quelldatensatz

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06248894B1