تفاعل #75433

معادلة التفاعل

10-undecene-1-ol

triphenylphosphine

phthalimide

Diethyl azodicarboxylate

→

1-phthalimidylundec-10-ene

المذيبات

tetrahydrofuran

THF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر