5-Butoxy-2-carboyxy-4-methyl-oxazol | 23429-13-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-Butoxy-2-carboyxy-4-methyl-oxazol
• 英文别名: 5-butoxy-4-methyl-oxazole-2-carboxylic acid；5-Butoxy-4-methyl-1,3-oxazole-2-carboxylic acid
• CAS: 23429-13-2
• 化学式: C₉H₁₃NO₄
• 分子量: 199.207
• InChiKey: WWYCYSQKLZHUCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-Butoxy-2-carboyxy-4-methyl-oxazol 以 水 为溶剂， 以55.2 g的产率得到5-丁氧基-4-甲基-1,3-恶唑
  参考文献：
  名称：

  Improved “Oxazole” Method for the Practical and Efficient Preparation of Pyridoxine Hydrochloride (Vitamin B₆)

  摘要：

  Vitamin 86, a well-studied vitamin B, has been synthesized using an oxazole method for the past 20 years. The oxazole method provided 56.2% overall yield but also generated safety, environmental, and health problems, such as using toxic benzene as solvent and unstable, corrosive, and pollutive HCl and POCl3 as reagents. To use the same equipment but the least amount of toxic agents, we developed new reaction conditions for the early steps. For example, we successfully replaced toxic HCl/benzene conditions with NaHSO4/PhCH3 conditions and also developed a novel and efficient dehydrating agent trichloroisocyanuric acid/Ph3P/Et3N to synthesize the key intermediate 5-butoxy-4-methyl oxazole, instead of using phosphorus oxychloride. These improvements resolved safety, waste avoidance, and workup issues that plagued the previous methodologies. Our process comprised six easy synthetic steps and generated vitamin B-6 with 99.4% purity in 56.4% overall yield.

  DOI：

  10.1021/op4001687
• 作为产物：
  描述：

  Butyl 5-butoxy-4-methyl-1,3-oxazole-2-carboxylate 在 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 0.5h， 生成 5-Butoxy-2-carboyxy-4-methyl-oxazol
  参考文献：
  名称：

  Improved “Oxazole” Method for the Practical and Efficient Preparation of Pyridoxine Hydrochloride (Vitamin B₆)

  摘要：

  Vitamin 86, a well-studied vitamin B, has been synthesized using an oxazole method for the past 20 years. The oxazole method provided 56.2% overall yield but also generated safety, environmental, and health problems, such as using toxic benzene as solvent and unstable, corrosive, and pollutive HCl and POCl3 as reagents. To use the same equipment but the least amount of toxic agents, we developed new reaction conditions for the early steps. For example, we successfully replaced toxic HCl/benzene conditions with NaHSO4/PhCH3 conditions and also developed a novel and efficient dehydrating agent trichloroisocyanuric acid/Ph3P/Et3N to synthesize the key intermediate 5-butoxy-4-methyl oxazole, instead of using phosphorus oxychloride. These improvements resolved safety, waste avoidance, and workup issues that plagued the previous methodologies. Our process comprised six easy synthetic steps and generated vitamin B-6 with 99.4% purity in 56.4% overall yield.

  DOI：

  10.1021/op4001687

文献信息

• The Synthetic Intermediate of Pyridoxine. I. A Novel Synthesis of 5-Alkoxy-2-carboxy-4-methyloxazole
  作者：Itsutoshi Maeda、Masahiro Takehara、Kazushi Togo、Soichiro Asai、Ryonosuke Yoshida

  DOI：10.1246/bcsj.42.1435

  日期：1969.5