Chlorotrimethylsilane → 1-(2-Dimethylaminoethoxy)-1-trimethylsiloxy-2-methyl-1-propene

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Reaction Conditions

Reaction Steps

To a solution of 31.78 g (44 mL, 0.314 mol) of diisopropylamine (Aldrich gold label) in 300 mL of tetrahydrofuran at -5° to 0° C. was added over a period of about 30 min. 0.314 mol of 1.6N n-butyl lithium in hexane (196 mL). After 30 min at 0° C., the solution was cooled to -78° C. and 50 g (0.314 mol) of 2-dimethylaminoethyl isobutyrate, prepared as above, was added keeping the temperature below -70° C. Then 34.11 g (39.9 mL, 0.314 mol) of chlorotrimethylsilane was added below -70° C. After warming to room temperature, the mixture was concentrated on a rotary evaporator, and the residue was treated with hexane and filtered under argon. The filtrate was concentrated on a rotary evaporator and distilled in a spinning band column to give 45.4 g of 1-(2-dimethylaminoethoxy)-1-trimethylsiloxy-2-methyl-1-propene, b.p. 39°-42.5° C. (0.5 mm). 1H-NMR (360 MHz, benzene-d6): 0.22 (s, 9 H, SiMe), 1.67 (s, 3 H, =CCH3), 1.77 (s, 3 H, =CCH3), 2.12 (s, 6 H, NCH3), 2.46 (t, J=6 Hz, 2 H, CH2N), 3.85 (t, J=6 Hz, 2 H, CH2O). Anal Calcd for C11H25O2SiN: C 57.09, H 10.89, N 6.05, Si 12.14. Found: C 57.27, H 11.11, N 6.17, Si 11.37. IR (neat): 1705 cm-1 (C=C), no C=O absorption.

Provenance & Evidence