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ChemicalBook CAS DataBase List TERT-BUTYL ETHYL MALONATE
32864-38-3

TERT-BUTYL ETHYL MALONATE synthesis

8synthesis methods
Ethyl hydrogen malonate

1071-46-1

tert-Butanol

75-65-0

TERT-BUTYL ETHYL MALONATE

32864-38-3

The general procedure for the synthesis of tert-butyl ethyl malonate from monoethyl malonate and tert-butanol was as follows: tert-butanol (2.8 mL, 37.8 mmol) was slowly added to a stirring solution of monoethyl malonate (5 g, 37.8 mmol) in acetonitrile (45 mL). Subsequently, a solution of DCC (8.58 g, 41.6 mmol) dissolved in acetonitrile (5 mL) was added dropwise to the reaction mixture over a period of 2 hours with continuous stirring. Upon completion of the reaction, the reaction mixture was filtered to remove insoluble by-products and the filtrate was concentrated to give 4.72 g (66% yield) of tert-butyl ethyl malonate. The product was analyzed by LCMS showing 189.11 (M + 1)+ with a purity of 93.4%.1H NMR (CDCl3) data were as follows: δ 4.2 (q, 2H), 3.3 (s, 2H), 1.4 (s, 9H), 1.3 (t, 3H).

-

Yield:32864-38-3 66%

Reaction Conditions:

with dicyclohexyl-carbodiimide in acetonitrile for 2 h;

Steps:

Synthesis of Malonic acid tert-butyl ester ethyl ester
Synthesis of Malonic acid tert-butyl ester ethyl ester tert-butanol (2.8 mL, 37.8 mmol) was added to a stirred solution of malonic acid monoethyl ester (5 g, 37.8 mmol) in acetonitrile (45 mL). DCC (8.58 g, 41.6 mmol) dissolved in acetonitrile (5 mL) was added dropwise with stirring over a period of 2 hours. The reaction mixture was filtered and the filtrate was concentrated to afford 4.72 g (66%) of malonic acid tert-butyl ester ethyl ester. LCMS: 189.11 (M+1)+ 93.4%, 1H NMR: (CDCl3): δ 4.2 (q, 2H), 3.3 (s, 2H), 1.4 (s, 9H), 1.3 (t, 3H).

References:

FOREST LABORATORIES HOLDINGS LIMITED US2009/239848, 2009, A1 Location in patent:Page/Page column 29

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