Reaktion #75433

Reaktionsgleichung

10-undecene-1-ol

triphenylphosphine

phthalimide

Diethyl azodicarboxylate

→

1-phthalimidylundec-10-ene

Lösungsmittel

tetrahydrofuran

THF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle