Reacción #75433

Ecuación de reacción

10-undecene-1-ol

triphenylphosphine

phthalimide

Diethyl azodicarboxylate

→

1-phthalimidylundec-10-ene

Disolventes

tetrahydrofuran

THF

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente