反应 #75433

反应方程式

10-undecene-1-ol

triphenylphosphine

phthalimide

Diethyl azodicarboxylate

→

1-phthalimidylundec-10-ene

溶剂

tetrahydrofuran

THF

反应条件

后处理

1. 1
   workup.ADDITIONadded dropwise by syringe
2. 2
   workup.ADDITIONAfter the addition
3. 3
   workup.STIRRINGthe reaction was stirred at room temperature for 4 hours
4. 4
   其他The solvent was evaporated under vacuum and ether (30 mL)
5. 5
   workup.ADDITIONwas added
6. 6
   其他to precipitate the triphenylphosphine oxide and hydrazine dicarboxylate which
7. 7
   其他were removed by filtration
8. 8
   洗涤The precipitate was rinsed with ether (2×30 mL)
9. 9
   其他the combined filtrates were evaporated
10. 10
    其他to afford a yellow solid
11. 11
    其他The yellow solid was triturated with warm hexanes (3×50 mL)
12. 12
    过滤filtered
13. 13
    其他The combined hexanes were evaporated

实验过程

A mixture of 10-undecene-1-ol (5.00 g, 29.36 mmol, 1 equiv), triphenylphosphine (7.70 g, 29.36 mmol, 1 equiv) and phthalimide (4.32 g, 29.36 mmol, 1 equiv) in dry tetrahydrofuran (THF, 30 mL) was stirred vigorously under argon. Diethyl azodicarboxylate (DEAD, 5.11 g, 29.36 mmol, 1 equiv) was diluted with THF (12 mL) and added dropwise by syringe. After the addition, the reaction was stirred at room temperature for 4 hours. The solvent was evaporated under vacuum and ether (30 mL) was added to precipitate the triphenylphosphine oxide and hydrazine dicarboxylate which were removed by filtration. The precipitate was rinsed with ether (2×30 mL) and the combined filtrates were evaporated to afford a yellow solid. The yellow solid was triturated with warm hexanes (3×50 mL) and filtered. The combined hexanes were evaporated to give 1-phthalimidylundec-10-ene as a yellow wax.

来源