Reaction #2389083

Reaction equation

10-undecene-1-ol

triphenylphosphine

phthalimide

Diethyl azodicarboxylate

→

1-phthalimidylundec-10-ene

Solvents

tetrahydrofuran

THF

Conditions

Workup

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

Procedure

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