10-Octadecenoic acid, methyl ester, (10Z)- synthesis
- Product Name:10-Octadecenoic acid, methyl ester, (10Z)-
- CAS Number:17257-43-1
- Molecular formula:C19H36O2
- Molecular Weight:296.49
26543-36-2
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17257-43-1
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Yield: 96%
Reaction Conditions:
with palladium, 5% on calcium carbonate, poisoned with lead;hydrogen in ethyl acetate at 20; for 0.583333 h;
Steps:
2.8.3 (Z)-Methyl octadec-10-enoate (7)
The acetylenic fatty acid ester 6 (107mg, 0.363mmol) was hydrogenated over 5% Pd/CaCO3 poisoned with Pb (67.8mg) in EtOAc (10mL) under H2 (balloon pressure) for 35min at rt. The mixture was filtered through a short column on silica gel and concentrated in vacuo to give olefin 7 (125mg, 0.420mmol, 96%) as a pale yellow oil. This was used for the next step without further purifications. 1H NMR (500MHz) δ 0.88 (3H, t, J=7.0Hz), 1.22-1.40 (20H, m), 1.55-1.68 (2H, m), 1.96-2.07 (4H, m), 2.30 (2H, t, J=7.6Hz), 3.66 (3H, s), 5.32-5.37 (2H, m). 13C NMR (125MHz) δ 14.10, 22.67, 24.95, 27.18, 27.20, 29.13, 29.22 (×2), 29.27, 29.33, 29.72, 29.76, 31.86, 34.10, 51.42, 129.80. 129.94, 174.33. DART-MS m/z (rel intensity) 298 (20), 297 (100). HR-DART-MS [M+H]+ m/z 297.28021 (calcd for C19H37O2: 297.27936).
References:
Ishibashi, Fumito;Kuwano, Kazuyoshi;Shibahara, Tomohiro;Zha, Shijiao [Fitoterapia,2020,vol. 145]
19220-39-4
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2777-65-3
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629-04-9
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55695-90-4
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