对甲苯磺酸 → 1-(2-Tetrahydropyranyloxy)-2-octadecanol

HRID 1123

反应方程式

HRID 1123 反应方程式
[CH2:1]([OH:20])[CH:2]([OH:19])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:32]1[CH:37]=[CH:36][CH2:35][CH2:34][CH2:33]1.C([O-])(O)=O.[Na+]>ClCCl>[O:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH:33]1[O:20][CH2:1][CH:2]([OH:19])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

参与物

6

反应物 4

HCID 6101对甲苯磺酸HCID 80803,4-二氢-2H-吡喃HCID 89314硬脂二醇HCID 516892碳酸氢钠

产物 1

HCID 196946481-(2-Tetrahydropyranyloxy)-2-octadecanol收率 29%

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂

实验过程

A 1-liter flask equipped with a stirrer and dropping funnel was charged with 20 g (70 mmol) of octadecane-1,2-diol, 0.7 g (3.5 mmol) of p-toluenesulfonic acid and 350 ml of dichloromethane. While stirring the contents at room temperature, 5.9 g (70 mmol) of dihydropyran were added dropwise. After stirring the mixture at room temperature for 30 minutes, it was neutralized with NaHCO3 and concentrated under reduced pressure, and the resultant residue was then purified by column chromatography on silica gel, thereby obtaining 7.5 g (yield[: 29%) of 1-(2-tetrahydropyranyloxy)-2-octadecanol. This compound was charged into a 200-ml flask equipped with a stirrer, to which 5.1 g (50 mmol) of triethylamine and 50 ml of dichloromethane were added. Further, 3.8 g (33 mmol) of methanesulfonyl chloride were added at room temperature with stirring. After the resultant mixture was stirred at room temperature for 14 hours, the reaction mixture was added with water and subjected to extraction with dichloromethane, and the solvent was distilled off under reduced pressure. The resultant residue and 15 ml of dimethylformamide was charged into a 100-ml flask equipped with a stirrer, to which 5.5 g (83 mmol) of NaN3 were added. The contents were stirred at 90° C. for 1.5 hours. After cooling the reaction mixture to room temperature, it was added with water and subjected to extraction with chloroform, followed by concentration under reduced pressure. Thereafter, the resultant residue was purified by column chromatography on silica gel, thereby obtaining 7.1 g (yield: 90%) of an azide intermediate.

后处理

  1. customA 1-liter flask equipped with a stirrer
  2. stirringAfter stirring the mixture at room temperature for 30 minutes
  3. concentrationconcentrated under reduced pressure
  4. customthe resultant residue was then purified by column chromatography on silica gel

来源与证据

ORD记录
ord-cb7b361a66f24faab6f6db5494adcd1b
来源数据集
uspto-grants-1998_03
专利号
US05723497

关联笔记

加载中…