ChemicalBook CAS DataBase List Ethyl (E)-hex-2-enoate

Ethyl (E)-hex-2-enoate synthesis

9synthesis methods

Product Name:Ethyl (E)-hex-2-enoate
CAS Number:27829-72-7
Molecular formula:C8H14O2
Molecular Weight:142.2

123-72-8 Synthesis

123-72-8
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$12.32/25ML

Ethyl (triphenylphosphoranylidene)acetate

1099-45-2
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$6.00/5g

27829-72-7
191 suppliers
$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]