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Iodine → 5-(2-Iodophenyl)-2-triphenylmethyltetrazole

HRID 466822
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 466822
[C:1]1([C:7]2[N:8]=[N:9][N:10]([C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.CCCCCC.[I:42]I>C1COCC1>[I:42][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[C:7]1[N:8]=[N:9][N:10]([C:12]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:11]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 807IodineHCID 8058HexaneHCID 32929595-Phenyl-2-trityltetrazoleHCID 178418339Butyllithium

Produkt 1

HCID 189543585-(2-Iodophenyl)-2-triphenylmethyltetrazoleAusbeute 44,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

To a solution of 0.5 g (1.3 mmoles) of 18a in 10 mL dry THF cooled to -20° C. under a nitrogen atmosphere was added dropwise with stirring 0.55 mL of 2.5M n-butyl lithium in hexane (1.4 mmoles). When addition was complete, the reaction was allowed to warm to -10° C. over one hour, held there one hour, then cooled to -78° C. After stirring a few minutes, 0.4 g (1.57 mmole) of I2 was added all at once, and stirring continued. After 1 hour the reaction mixture was allowed to warm to ambient temperature. After removal of the solvent, the residue was partitioned between CHCl3 and 1M KH2PO4. The aqueous phase was extracted two more times, the combined organic phases washed with sufficient aqueous Na2S2O3 to remove excess I2, dried (MgSO4) and the solvent evaporated. The residue was crystallized from CH2Cl2 /ether to give 0.3 g product,

Aufarbeitung

  1. additionwas added dropwise
  2. additionWhen addition
  3. temperaturecooled to -78° C
  4. stirringstirring
  5. waitAfter 1 hour the reaction mixture was allowed
  6. temperatureto warm to ambient temperature
  7. customAfter removal of the solvent
  8. customthe residue was partitioned between CHCl3 and 1M KH2PO4
  9. extractionThe aqueous phase was extracted two more times
  10. washthe combined organic phases washed with sufficient aqueous Na2S2O3
  11. customto remove excess I2
  12. dry with materialdried (MgSO4)
  13. customthe solvent evaporated
  14. customThe residue was crystallized from CH2Cl2 /ether

Quellen und Nachweise

ORD-Eintrag
ord-8c63c4fd92044c4b84daf7e2e491b3be
Quelldatensatz
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05157040

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