10-Octadecynoic acid methyl ester synthesis
- Product Name:10-Octadecynoic acid methyl ester
- CAS Number:26543-36-2
- Molecular formula:C19H34O2
- Molecular Weight:294.47
Yield:26543-36-2 100%
Reaction Conditions:
in methanol;diethyl ether;dichloromethane at 20;
Steps:
2.8.2 Methyl octadec-10-ynoate (6)
To a solution of 5 (123mg, 0.440mmol) in a mixture of CH2Cl2 (6mL) and MeOH (6mL), was added 2M ethereal solution of TMSCH2N2 (0.9mL, 1.8mmol) and the mixture was stirred at rt. until TLC revealed the disappearance of the acid. The reaction was then quenched with one drop AcOH and the solvent was removed in vacuo to afford 6 (129mg, 0.439mmol, 100%) as a colorless oil. This was used for the next step without further purifications. 1H NMR (300MHz) δ 0.88 (3H, t, J=7.0Hz), 1.23-1.41 (16H, m), 1.41-1.54 (4H, m), 1.58-1.70 (2H, m), 2.14 (4H, t, J=7.0), 2.30 (2H, t, J=7.6Hz), 3.67 (3H, s).
References:
Ishibashi, Fumito;Kuwano, Kazuyoshi;Shibahara, Tomohiro;Zha, Shijiao [Fitoterapia,2020,vol. 145]
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