Ethyl Acetate → T-Butyl(1-Ethoxyvinyloxy)Dimethylsilane

To a solution of 2,2,6,6-tetramethylpiperidine (17.34 mL, 102.14 mmol) in THF (63.4 mL) under argon, 2.9 M BuLi in hexanes (34.05 mL, 98.74 mmol) was added dropwise at 0° C. The reaction was stirred for 15 min. and subsequently cooled to −78° C. t-Butyldimethylchlorosilane (TBDMSCl) (16.94 g, 112.36 mmol) in THF (25.4 mL) was added and then a solution of anhydrous ethyl acetate (8.38 mL, 85.12 mmol) in THF (57.2 mL) was slowly added over 1 h. The mixture was stirred for an additional 10 min at −78° C. and then stirred at r.t. for 1 h. The solution was then diluted with hexanes (285.9 mL), filtered through a Celite pad, and the filtrate concentrated. Distillation under vacuum at 42-50° C. gave an orange oil (g, 2.0%). 1H NMR (400 MHz, CDCl3) δ 3.74 (q, 2H, J=7.0 Hz, CH2), 3.22 (d, 1H, J=2.0 Hz, CH2), 3.05 (d, 1H, J=2.0 Hz, CH2), 1.29 (t, 3H, J=7.1 Hz, CH3), 0.94 (s, 9H, CH3), 0.17 (s, 6H, CH3); 13C NMR (400 MHz, CDCl3) δ 160.3, 62.4, 59.6, 24.79, 17.3, 13.5, −5.4

1. additionwas added
2. stirringThe mixture was stirred for an additional 10 min at −78° C.
3. stirringstirred at r.t. for 1 h
4. filtrationfiltered through a Celite pad
5. concentrationthe filtrate concentrated
6. distillationDistillation under vacuum at 42-50° C.
7. customgave an orange oil (g, 2.0%)

ORD record

ord-b592ff1f413c44dea873b0510f50d348

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969622B2