NSC71618 synthesis
- 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]
64354-19-4
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24317-96-2
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110-59-8
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24317-96-2
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93-89-0
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$13.00/100g
24317-96-2
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