DIETHYL 2-(3,4-DICHLOROPHENYL)MALONATE synthesis
- Product Name:DIETHYL 2-(3,4-DICHLOROPHENYL)MALONATE
- CAS Number:28751-26-0
- Molecular formula:C13H14Cl2O4
- Molecular Weight:305.15
6725-45-7
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$12.00/5g
105-58-8
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28751-26-0
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$56.29/1g
Yield:28751-26-0 100%
Reaction Conditions:
with sodium hydride in tetrahydrofuran;mineral oil; for 2 h;Reflux;
Steps:
5 5.5 Diethyl(3,4-dichlorophenyl)propanedioate (26a)
To a solution of ethyl 2-(3,4-dichlorophenyl)acetate (5.0g, 21mmol) in THF (60mL) were added NaH (60% in oil, 1.7g, 43mmol) and diethyl carbonate (13mL, 110mmol) at room temperature. After being refluxed for 2h, the reaction mixture was quenched with satd NH4Cl aq and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give 26a (6.6g, 100%) as a pale yellow oil. 1H NMR (CDCl3) δ: 1.25-1.33 (6H, m), 4.11-4.28 (4H, m), 4.54 (1H, s), 7.24-7.27 (1H, m), 7.43 (1H, d, J=8.1Hz), 7.51 (1H, d, J=2.4Hz).
References:
Takai, Takafumi;Koike, Tatsuki;Nakamura, Minoru;Kajita, Yuichi;Yamashita, Toshiro;Taya, Naohiro;Tsukamoto, Tetsuya;Watanabe, Tomomichi;Murakami, Koji;Igari, Tomoko;Kamata, Makoto [Bioorganic and Medicinal Chemistry,2016,vol. 24,# 14,p. 3192 - 3206]
