Triphenylundecylphosphonium bromide → HCID 54242059, Verbindung

HRID 1756949Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1756949
[Li]CCCC.[Br-].[CH2:7]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[CH:37]([C:39]1[CH:40]=[N:41][N:42]([CH:44]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH:43]=1)=O>C1COCC1>[CH:37]([C:39]1[CH:40]=[N:41][N:42]([CH:44]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH:43]=1)=[CH:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH3:7]

Komponenten

5

Edukt 3

HCID 3085198Triphenylundecylphosphonium bromideHCID 10563150ethyl (+/-)-4-formyl-alpha-phenyl-1H-pyrazole-l-acetateHCID 178418339Butyllithium

Produkt 1

HCID 54242059HCID 54242059, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of n-BuLi (127 mL, 254 mmol, 2.0M in hexanes) was added dropwise to a suspension of n-undecyl-triphenylphosphonium bromide (121.6 g, 244 mmol, obtained from triphenylphosphine and undecylbromide) in 500 mL THF at -78° C. under an atmosphere of N2. The resulting orange solution was stirred for 1 hour before a solution of ethyl (±)-4-formyl-α-phenyl-1H-pyrazole-1-acetate in 250 mL THF was added dropwise. Warmed to room temperature and stirred for 16 hours. Quenched by adding 150 mL water and concentrating in vacuo. The residue was partitioned between water and dichloromethane. The organic layer was dried over MgSO4, filtered, and concentrated to give an oily tan solid. Triturated with boiling hexanes and filtered to remove triphenylphosphine oxide. The filtrate was concentrated and chromatographed (10% EtOAc/hexanes on silica) to give the title compound as a yellow oil, a 1:2 E/Z mixture (44.4 g, 50%).

Aufarbeitung

  1. additionwas added dropwise
  2. customQuenched
  3. additionby adding 150 mL water
  4. concentrationconcentrating in vacuo
  5. customThe residue was partitioned between water and dichloromethane
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give an oily tan solid
  10. customTriturated with boiling hexanes
  11. filtrationfiltered
  12. customto remove triphenylphosphine oxide
  13. concentrationThe filtrate was concentrated
  14. customchromatographed (10% EtOAc/hexanes on silica)

Quellen und Nachweise

ORD-Eintrag
ord-c4de1ad2990442318a9ae27313a6992b
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05441975

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