Phthalimide → 2-(Undec-10-en-1-yl)-1H-isoindole-1,3(2H)-dione

HRID 47155

Reaktionsgleichung

Reaktionsgleichung von HRID 47155
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:32]1(=[O:42])[NH:36][C:35](=[O:37])[C:34]2=[CH:38][CH:39]=[CH:40][CH:41]=[C:33]12.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:32]1(=[O:42])[N:36]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11])[C:35](=[O:37])[C:34]2=[CH:38][CH:39]=[CH:40][CH:41]=[C:33]12

Komponenten

6

Edukt 4

HCID 6809PhthalimideHCID 818510-Undecen-1-olHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Produkt 1

HCID 220445222-(Undec-10-en-1-yl)-1H-isoindole-1,3(2H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-6138fbfac24d447199213a4fb085e741
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699467B2

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