Diisopropylamine → (1-tert-Butoxy-vinyloxy)-tert-butyl-dimethyl-silane

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 58.2 g diisopropylamine (575 mmol) in 500 ml tetrahydrofuran were added at 0° C. 344 ml 1.6M BuLi in hexane (550 mmol) over 20 min. After stirring for 15 min the solution was cooled to −70° C. and 58.1 g tert-butyl acetate (500 mmol; Fluka) were added at −70° C. over 15 min and stirring continued for 15 min. After the addition of 75 ml HMPA (Fluka) a solution of 81.6 g tert-butyldimethylchlorosilane (525 mmol; Fluka) in 100 ml tetrahydrofuran was added at −70° C. over 15 min and the reaction mixture was warmed to RT over ˜1 h. The reaction mixture was concentrated by rotary evaporation (40° C./≧10 mbar) and the honey-oily residue was partitioned between 1000 ml hexane and 1000 ml deionized water. The organic layer was washed with 10% brine (2×500 ml) and dried (Na2SO4) affording after removal of the solvent by rotary evaporation (40° C./≧10 mbar) 116.1 g bright yellow oil. Purification by vacuum distillation gave 106.0 g (92.0%) product as a colorless oil, b.p. 53-54° C./2.0 mbar. 1H-NMR:

Provenance & Evidence