ChemicalBook CAS DataBase List 2-[(2-Chlorophenyl)Methylene]-4-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethoxy]-3-oxobutanoic Acid Ethyl Ester

2-[(2-Chlorophenyl)Methylene]-4-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethoxy]-3-oxobutanoic Acid Ethyl Ester synthesis

5synthesis methods

Product Name:2-[(2-Chlorophenyl)Methylene]-4-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethoxy]-3-oxobutanoic Acid Ethyl Ester
CAS Number:400024-08-0
Molecular formula:C23H20ClNO6
Molecular Weight:441.86

89-98-5 Synthesis

89-98-5
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88150-75-8 Synthesis

ETHYL4-[2-(1,3-DIOXO-1,3-DIHYDRO-2H-ISOINDOL-2-YL)ETHOXYL]-3-OXOBUTANOATE

88150-75-8
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2-[(2-Chlorophenyl)Methylene]-4-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethoxy]-3-oxobutanoic Acid Ethyl Ester

400024-08-0
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Yield:400024-08-0 56%

Reaction Conditions:

with pyrrolidine;acetic acid in isopropyl alcohol at 37; for 5 h;

Steps:

11 EXAMPLE 11; Preparation of ethyl-2-(2-chlorobenzylidine)-4-[2-(phthalimido)ethoxy]acetoacetate (XVIII)

Preparation of ETHYL 2-(2-CHLOROBENZYLIDINE)-4-[2-(PHTHALIMIDE) ETHOXY] ACETOACETATE (XV : A 250 mL two-necked flask, equipped with a magnetic stirring bar and thermometer was charged with 10 g of ethyl 4- [2- (phthalimido) ethoxy] acetoacetate and 3.96 g 2- chlorobenzaldehyde and 100 mL isopropanol under nitrogen atmosphere. To the resulting mixture was added 0.188 ML of acetic acid and 0.223 ML pyrolidine. The reaction mixture was heated to 37 °C and stirred at this temperature for 5 hours. The solvent was removed in vacuo and the residue was dissolved in 100 ML of methylene chloride. The resulting solution was washed with 100 mL of sat. NAHCO3 and 100 mL of water, dried over 5 G OF MGS04. MGS04 was filtered off, the filtrate was concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate/hexane (20/80) as an eluent to give 7.72 g of ethyl 2- (2-CHLOROBENZYLIDINE)-4- [2- (PHTHALIMIDE) ethoxy] acetoacetate as an light brown oil (yield 56%, rel. compound purity > 98%). 1H-NMR (CDCL3) No. 7.89 (s, 1H), 7.78 (dd, 2H), 7.69 (dd, 2H), 7.35 (M, 1H), 7.28 (M, 2H), 7.17 (M, 1H), 4.44 (s, 2H), 4.05 (Q, 2H), 3.76 (T, 2H), 3.64 (t, 2H), 1.20 (t, 3H). 13C-NMR (CDCI3) 6 203. 2,168. 4,164. 0,140. 0,134. 0,133. 9,132. 3,131. 5, 130.4, 129.8, 127.3, 126.8, 123.4, 77.7, 68.5, 62.0, 37.4, 14.3.

References:

WO2004/58711,2004,A1 Location in patent:Page 20

3891-07-4 Synthesis