反应详情

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.

1. additionadded dropwise by syringe
2. additionAfter the addition
3. stirringthe reaction was stirred at room temperature for 4 hours
4. customThe solvent was evaporated under vacuum and ether (30 mL)
5. additionwas added
6. customto precipitate the triphenylphosphine oxide and hydrazine dicarboxylate which
7. customwere removed by filtration
8. washThe precipitate was rinsed with ether (2×30 mL)
9. customthe combined filtrates were evaporated
10. customto afford a yellow solid
11. customThe yellow solid was triturated with warm hexanes (3×50 mL)
12. filtrationfiltered
13. customThe combined hexanes were evaporated