tert-butyl(2-(2-chloroethoxy)ethoxy)dimethylsilane synthesis

Yield:119382-85-3 99%

Reaction Conditions:

with 1H-imidazole in tetrahydrofuran at 0 - 20; for 16 h;

Steps:

344.1 Step 1. Synthesis of tert-butyl[2-(2-chloroethoxy)ethoxy]dimethylsilane

Step 1.
Synthesis of tert-butyl[2-(2-chloroethoxy)ethoxy]dimethylsilane
To a solution of 2-(2-chloroethoxy)ethanol (3.00 mL, 28.4 mmol) in THF (120 mL) was added tert-butyldimethylsilyl chloride (5.56 g, 36.9 mmol) and imidazole (2.90 g, 42.6 mmol) at 0° C.
The reaction mixture was stirred at room temperature for 16 h.
The solution was concentrated.
The residue was treated with 1.0 N HCl_(aq) and extracted with CH₂Cl₂.
The combined organic layers were dried over MgSO_4(s), filtered, and concentrated to give tert-butyl[2-(2-chloroethoxy)ethoxy]dimethylsilane (6.75 g, 99%) as colorless oil which was directly used to next step without further purification. ¹H NMR (CDCl₃, 300 MHz) δ 3.79-3.74 (m, 4H), 3.64-3.57 (m, 4H), 0.89 (s, 9H), 0.07 (s, 6H).

References:

US2017/253569,2017,A1 Location in patent:Paragraph 0952-0953