High yield total syntheses of XH-14 derivatives using Sonogashira coupling reaction was written by Bang, Hyun Bae;Han, Su Young;Choi, Da Hye;Hwang, Jung Woon;Jun, Jong-Gab. And the article was included in ARKIVOC (Gainesville, FL, United States) in 2008.Synthetic Route of C11H16O3 This article mentions the following:
A method for the title compounds is reported here. XH-14 [i.e., 2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-3-benzofurancarboxaldehyde salvinal] is isolated from the root of Salvia miltiorrhiza Bunge (Chinese DanShen). A high yielding synthetic route to XH-14 derivatives is described using a Sonogashira reaction as a key step. Introduction of iodine into the structure and optimization of the synthetic sequence were essential for the successful syntheses of XH-14 derivatives The nine-step reaction sequence gave 2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-5-methoxy-3-benzofurancarboxaldehyde and 2-(4-hydroxy-3-methoxyphenyl)-6-(3-hydroxypropyl)-5-methoxy-3-benzofurancarboxaldehyde in 30% and 55% overall yields, resp. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Synthetic Route of C11H16O3).
3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. But on the other hand, ethers undergo cleavage by reaction with acids. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly autoxidize to form hydroperoxides and dialkyl peroxides. If concentrated or heated, these peroxides may explode. To prevent such explosions, ethers should be obtained in small quantities, kept in tightly sealed containers, and used promptly.Synthetic Route of C11H16O3
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem