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ChemicalBook CAS DataBase List (2-{2-[2-(Toluene-4-sulfonyloxy)-ethoxy]-ethoxy}-ethoxy)-acetic acid tert-butyl ester

(2-{2-[2-(Toluene-4-sulfonyloxy)-ethoxy]-ethoxy}-ethoxy)-acetic acid tert-butyl ester synthesis

8synthesis methods
-

Yield: 82.1%

Reaction Conditions:

with pyridine at 20; for 16 h;

Steps:

10.10 Step 10: Synthesis of tert-butyl 2-(2-(2-(2-(tosyloxy)ethoxy)ethoxy)ethoxy)acetate (17)
To a mixture of tert-butyl 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]acetate (1 g, 3.78 mmol) in pyridine (10 mL), 4-methylbenzenesulfonyl chloride (1.08 g, 5.68 mmol) was added, The mixture was stirred at 20 °C for 16 hours. According to the LCM, the main peak of the desired mass appeared. TLC (petroleum ether/ethyl acetate=1:1) showed a main spot was formed. The mixture was poured into water (20 mL) and extracted with ethyl acetate (30 mL). The organic layer was washed with 1 N HCl aqueous solution (20 mL), It was dried over anhydrous Na2SO4 and concentrated. The residue was purified by chromatography (silica gel, eluting with petroleum ether/ethyl acetate=5:1 to 1:1) to give the title compound (1.3 g, 3.11 mmol, 82.10% yield) as a colorless oil.

References:

Eop Te Ra Co., Ltd.;Ryu Su-hui;Lee Hwa-jin;Kim Seong-hun;Ryu Hye-guk;Lee Eun-bin KR102160377, 2020, B1 Location in patent:Paragraph 0461; 0496-0499

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