Réaction #75433

Équation de réaction

10-undecene-1-ol

triphenylphosphine

phthalimide

Diethyl azodicarboxylate

→

1-phthalimidylundec-10-ene

Solvants

tetrahydrofuran

THF

Conditions de réaction

Traitement

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
   AutreThe solvent was evaporated under vacuum and ether (30 mL)
5. 5
   workup.ADDITIONwas added
6. 6
   Autreto precipitate the triphenylphosphine oxide and hydrazine dicarboxylate which
7. 7
   Autrewere removed by filtration
8. 8
   LavageThe precipitate was rinsed with ether (2×30 mL)
9. 9
   Autrethe combined filtrates were evaporated
10. 10
    Autreto afford a yellow solid
11. 11
    AutreThe yellow solid was triturated with warm hexanes (3×50 mL)
12. 12
    Filtrationfiltered
13. 13
    AutreThe combined hexanes were evaporated

Mode opératoire

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.

Source