N,N,N',N'-Tetramethylethylenediamine → N,N-diethyl-2-[(chloromethyl)dimethylsilyl]-1-naphthalenecarboxamide

A solution of 1.3M s-BuLi in cyclohexane (20.3 mL, 26.4 mmol) was added dropwise to an ether/liquid nitrogen-cooled solution of TMEDA (4.0 mL, 26.5 mmol) in THF (15 mL), maintaining the internal reaction temperature <-80° C. To this mixture was added a solution of N,N-diethyl-1-naphthalenecarboxamide (5.0 g, 22.0 mmol) in THF (10 mL), again maintaining the internal reaction temperature <-80° C. The resulting solution was stirred with dry ice/acetone cooling for 30 min, then was recooled to <-80° C. with an ether/liquid nitrogen bath while chloromethyl dimethylsilyl chloride (3.8 mL, 28.8 mmol) was added dropwise. The mixture was warmed to RT to afford a green solution which was diluted with ether and extracted with dilute aq citric acid (2 X), followed with sat aq NaHCO3. The ether solution was dried (MgSO4), concentrated, and chromatographed with 3:17 ethyl acetate/hexanes to afford 4.3 g of N,N-diethyl-2-[(chloromethyl)dimethylsilyl]-1-naphthalenecarboxamide as a yellow oil, a 59% yield.

1. temperaturemaintaining the internal reaction temperature <-80° C
2. temperatureagain maintaining the internal reaction temperature <-80° C
3. additionwas added dropwise
4. customto afford a green solution which
5. extractionextracted with dilute aq citric acid (2 X)
6. dry with materialThe ether solution was dried (MgSO4)
7. concentrationconcentrated
8. customchromatographed with 3:17 ethyl acetate/hexanes

ORD-Eintrag

ord-835f14c80df74bd994ba507692370cad

Quelldatensatz

uspto-grants-1999_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05994270