Ethyl (E)-hex-2-enoate synthesis
- Product Name:Ethyl (E)-hex-2-enoate
- CAS Number:27829-72-7
- Molecular formula:C8H14O2
- Molecular Weight:142.2
123-72-8
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1099-45-2
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27829-72-7
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$16.00/10g
Yield:27829-72-7 72%
Reaction Conditions:
in dichloromethane at 20; for 47 h;Inert atmosphere;Wittig Olefination;
Steps:
Synthesis and data for (E)-ethyl hex-2-enoate (6):
To a stirred solution of butanal(0.213 g, 2.95 mmol) in CH2Cl2 (15 mL) under an atmosphere of nitrogen wasadded (carbethoxymethylene)triphenylphosphorane (1.24 g, 3.50 mmol) andthe resulting mixture stirred for 47 h. The solvent was removed in vacuo,without application of heat, and pentane (30 mL) was added to the residue,which was then stirred for 30 min. The resulting mixture was filtered, thesolvent removed in vacuo, without application of heat, and the crude productwas purified using flash chromatography (95:5 pentane/Et2O) to give the ester6 (0.30 g, 72%) as a pale yellow oil. dH (400 MHz, CDCl3): 0.93 (3H, t, J = 7.5 Hz,6-CH3), 1.28 (3H, t, J = 7.0 Hz, 8-CH3), 1.44-1.53 (2H, m, 5-CH2), 2.14-2.20 (2H,m, 4-CH2), 4.18 (2H, q, J = 7.0 Hz, 7-CH2), 5.81 (1H, dt, J = 1.5, 15.9 Hz, 2-H), 6.96(1H, dt, J = 7.1, 15.2 Hz, 3-H); dC (100 MHz, CDCl3): 13.8 (C-6), 14.4 (C-8), 21.4(C-5), 34.3 (C-4), 60.2 (C-7), 121.5 (C-2), 149.3 (C-3), 166.9 (C-1).
References:
Duhamel, Nina;Piano, Federico;Davidson, Samuel J.;Larcher, Roberto;Fedrizzi, Bruno;Barker, David [Tetrahedron Letters,2015,vol. 56,# 13,p. 1728 - 1731]
6728-26-3
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64-17-5
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27829-72-7
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867-13-0
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123-72-8
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27829-72-7
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2396-84-1
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123-66-0
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27829-72-7
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26553-46-8
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64187-83-3
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123-72-8
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$12.32/25ML
27829-72-7
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13419-69-7
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