反应 #2348134

反应方程式

5,9,13-trimethyl-1-tetradecanol

pyridine

p-toluenesulfonyl chloride

→

(5,9,13-trimethyltetradecyl)tosylate

收率 76.2%

溶剂

methylene chloride

methylene chloride

反应条件

后处理

1. 1
   workup.ADDITIONAfter the dropwise addition
2. 2
   其他the resulting reaction solution
3. 3
   洗涤was successively washed with 200 ml of water, 200 ml of 2N hydrochloric acid, and 200 ml of a saturated sodium bicarbonate water
4. 4
   干燥was dried over anhydrous magnesium sulfate
5. 5
   过滤After the filtration
6. 6
   浓缩the resultant was concentrated under reduced pressure

实验过程

Under a nitrogen atmosphere, a solution of 27 g (0.11 mol) of 5,9,13-trimethyl-1-tetradecanol and 10 g (0.13 mol) of pyridine in 200 ml of dry methylene chloride was added dropwise to a solution of 22.1 g (0.12 mol) of p-toluenesulfonyl chloride in 100 ml of dry methylene chloride under ice cooling. After the dropwise addition, the mixture was agitated at room temperature overnight, the resulting reaction solution was successively washed with 200 ml of water, 200 ml of 2N hydrochloric acid, and 200 ml of a saturated sodium bicarbonate water, and was dried over anhydrous magnesium sulfate. After the filtration, the resultant was concentrated under reduced pressure to obtain 34.4 g of (5,9,13-trimethyltetradecyl)tosylate. Under a nitrogen gas stream, 25.8 g (0.21 mol) of erythritol was dissolved in 200 ml of dry DMF, and 4.2 g (0.11 mol) of 60% NaH was added in several batches under ice cooling. After the addition, the resultant was agitated at room temperature for 1 hour, and then was heated to 50° C. A half amount of (5,9,13-trimethyltetradecyl)tosylate obtained above (17.2 g) was added dropwise thereto, and was washed with 55 ml of DMF. The resultant was heated to 80° C. and then agitated for 4 hours, the resulting reaction solution was concentrated under reduced pressure, 500 ml of ether was added to the residual solution to perform extractive dissolution twice, the product was washed twice with saturated saline, and then it was dried over anhydrous magnesium sulfate. After the filtration, the resultant was concentrated, and purified by silica gel column chromatography to obtain 2.3 g of 1-O-(5,9,13-trimethyltetradecyl)erythritol having the following properties. As a result of HPLC analysis of the obtained product, the purity of 1-O-(5,9,13-trimethyltetradecyl)erythritol was 76.9% and that of 2-O-(5,9,13-trimethyltetradecyl)erythritol was 23.1%. The results of NMR analysis are as shown below.

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