ChemicalBook CAS DataBase List NSC71618

NSC71618 synthesis

9synthesis methods

Product Name:NSC71618
CAS Number:24317-96-2
Molecular formula:C14H18O3
Molecular Weight:234.29

5459-35-8
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5908-41-8
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557-20-0
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24317-96-2
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Yield:24317-96-2 92%

Reaction Conditions:

in n-heptane;dichloromethane at 20; for 18 h;Inert atmosphere;

Steps:

6 4.2.6. Ethyl 2-benzoylpentanoate (5a).

Diethylzinc (0.56 mL, 1 M in heptane, 2 equiv) was added under argon to a room-temperature solution of 2-bromo-acrylic acid ethyl ester (50 mg, 0.279 mmol, 1 equiv) and benzoyltrimethylsilane (55 mg, 0.307 mmol, 1.1 equiv) in non-degassed dichloromethane (1.4 mL). After 18 h at room temperature, the reaction was quenched with saturated NH₄Cl. The layers were separated and the aqueous layer was extracted twice with CH₂Cl₂. The combined organic phases were dried (MgSO₄), filtered and concentrated in vacuo. After purification by flash chromatography on silica gel (pentane/ethyl acetate from 100/0 to 98/2) 5a was isolated as a colorless oil (60 mg, 0.26 mmol, 92%). ¹H NMR (400 MHz, CDCl₃) δ: 0.94 (3H, t, J=7.3), 1.16 (3H, t, J=7.3), 1.33-1.44 (2H, m), 1.91-2.06 (2H, m), 4.14 (2H, AB part of a ABX₃ pattern), 4.30 (1H, t, J=7.3), 7.43-7.51 (2H, m), 7.55-7.61 (1H, m), 7.96-8.01 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 14.0 (CH₃), 14.1 (CH₃), 21.0 (CH₂), 31.1 (CH₂), 54.3 (CH), 61.4 (CH₂), 128.7 (2×=CH), 128.8 (2×=CH), 133.5 (=CH), 136.5 (=C) 170.2 (C=O), 195.4 (C=O). HRMS (ESI): m/z: calcd for [MH⁺] C₁₄H₁₉O₃: 235.1329; found: 235.1330.

References:

Vibert, Fran?ois;Maury, Julien;Lingua, Hugo;Besson, Eric;Siri, Didier;Bertrand, Michèle P.;Feray, Laurence [Tetrahedron,2015,vol. 71,# 47,p. 8991 - 9002]