반응 #2389083

반응 방정식

10-undecene-1-ol

triphenylphosphine

phthalimide

Diethyl azodicarboxylate

→

1-phthalimidylundec-10-ene

용매

tetrahydrofuran

THF

반응 조건

후처리

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

실험 절차

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.

출처