反応 #2348137

反応方程式

pentaerythritol

NaH

phytanyl tosylate

→

mono-O-(3,7,11,15-tetramethylhexadecyl)pentaerythritol

収率 22.8%

溶媒

DMF

反応条件

後処理

1. 1
   洗浄by washing with 55 ml of DMF
2. 2
   温度The resultant was heated to 80° C.
3. 3
   workup.STIRRINGagitated for 4 hours
4. 4
   その他the resulting reaction solution
5. 5
   濃縮was concentrated under reduced pressure, 500 ml of ether
6. 6
   workup.ADDITIONwas added to the residual solution
7. 7
   workup.DISSOLUTIONdissolution twice
8. 8
   洗浄the product was washed twice with saturated saline
9. 9
   乾燥it was dried over anhydrous magnesium sulfate
10. 10
    ろ過After the filtration
11. 11
    濃縮the resultant was concentrated
12. 12
    その他purified by silica gel column chromatography

実験手順

Under a nitrogen gas stream, 36.09 g (265.1 mmol) of pentaerythritol was dissolved in 210 ml of dry DMF, and 5.3 g (132.5 mmol) of 60% NaH was added little by little under ice cooling. The resultant was heated to room temperature and agitated for 1 hour, and 30.0 g (66.26 mmol) of phytanyl tosylate was added dropwise thereto, followed by washing with 55 ml of DMF. The resultant was heated to 80° C. and 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, purified by silica gel column chromatography to obtain 6.3 g of mono-O-(3,7,11,15-tetramethylhexadecyl)pentaerythritol, which was in colorless, transparent, and somewhat viscous liquid form. The purity of the product determined by HPLC analysis was not lower than 99.5%. The results of NMR analysis are as shown below.

出典