Statistics shows that Ethyl E-hex-2-enoate is playing an increasingly important role. we look forward to future research findings about 27829-72-7.
Application of 27829-72-7, These common heterocyclic compound, 27829-72-7, name is Ethyl E-hex-2-enoate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
To ester 6 (1.97 g, 14.86 mmol) in 9:1H2O/MeOH (100 mL), NaHSO3 (40percent w/v aqueous solution, 4.33 mL,16.64 mmol) and Et3N (2.31 mL, 16.64 mmol) were added. The resultingmixture was heated at reflux for 18 h. The solvent was removed in vacuo, andthe crude product was purified using flash chromatography (10:90:1 to20:80:1, MeOH/CH2Cl2/AcOH) to give acid 7 in 31percent yield as a yellow gum. dH(400 MHz; D2O): 0.94 (3H, t, J = 7.4 Hz, 6-CH3), 1.30 (18H, t, J = 7.3 Hz,(N(CH2CH3)3)2) 1.39?1.61 (3H, m, 5-CH2, 4-Ha), 1.83?1.92 (1H, m, 4-Hb), 2.56(1H, dd, J = 6.9, 16.1 Hz, 2-Ha), 2.81 (1H, dd, J = 6.4, 16.1 Hz, 2-Hb), 3.22 (12H, q,J = 7.5 Hz, (N(CH2CH3)3)2), 3.26?3.33 (1H, m, 3-H); dC (100 MHz; D2O) 8.8((N(CH2CH3)3)2), 13.8 (C-6), 20.2 (C-5), 32.7 (C-4), 36.7 (C-2), 47.3((N(CH2CH3)3)2), 57.6 (C-3), 178.2 (C-1); IR: mmax cm1 2987, 2704, 1716,1565, 1389, 1228, 1148; HRMS (ESI) found [MH2(Et3N)]+ 195.0333,C6H11O5S, required 195.0332. In a second fraction was obtained ester 8 (1.20 g,25percent) as a yellow oil. 1H (400 MHz; D2O): 0.95 (3H, t, J = 7.3 Hz, 6-CH3), 1.28?1.32 (12H, m, OCH2CH3, N(CH2CH3)3), 1.38?1.46 (1H, m, 4-Ha), 1.48?1.59 (2H,m, 5-CH2), 1.88?1.89 (1H, m, 4-Hb), 2.65?2.81 (2H, m, 2-CH2), 3.23 (6H, q,J = 7.2 Hz, N(CH2CH3)3), 3.31?3.36 (1H, m, 3-H), 4.20 (2H, q, J = 7.2 Hz,OCH2CH3); 13C (100 MHz; D2O): 8.2 (N(CH2CH3)3), 13.1 (C-6 and OCH2CH3),19.5 (C-5), 31.8 (C-4), 35.4 (C-2), 46.7 (N(CH2CH3)3), 56.8 (C-3), 62.1(OCH2CH3), 177.0 (C-1); IR: mmax cm1 2964, 2708, 1723, 1468, 1375, 1224;HRMS (ESI). Found [MHEt3N]+ 223.0652, C8H15O5S, required 223.0646.
Statistics shows that Ethyl E-hex-2-enoate is playing an increasingly important role. we look forward to future research findings about 27829-72-7.
Reference:
Article; Duhamel, Nina; Piano, Federico; Davidson, Samuel J.; Larcher, Roberto; Fedrizzi, Bruno; Barker, David; Tetrahedron Letters; vol. 56; 13; (2015); p. 1728 – 1731;,
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