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1-(3-Tert-butyldiphenylsilyloxymethyl-2,4-dichlorophenyl)-2-cyanopyrrole → 2-Aminomethyl-1-(3-tert-butyldiphenylsilyloxymethyl-2,4-dichlorophenyl)pyrrole

HRID 365574
Notizen
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Reaktionsgleichung

Reaktionsgleichung von HRID 365574
[Si:1]([O:18][CH2:19][C:20]1[C:21]([Cl:34])=[C:22]([N:27]2[CH:31]=[CH:30][CH:29]=[C:28]2[C:32]#[N:33])[CH:23]=[CH:24][C:25]=1[Cl:26])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH2:33][CH2:32][C:28]1[N:27]([C:22]2[CH:23]=[CH:24][C:25]([Cl:26])=[C:20]([CH2:19][O:18][Si:1]([C:14]([CH3:16])([CH3:15])[CH3:17])([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:21]=2[Cl:34])[CH:31]=[CH:30][CH:29]=1
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Komponenten

4

Edukt 2

HCID 183218191-(3-Tert-butyldiphenylsilyloxymethyl-2,4-dichlorophenyl)-2-cyanopyrroleHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 183217752-Aminomethyl-1-(3-tert-butyldiphenylsilyloxymethyl-2,4-dichlorophenyl)pyrroleAusbeute 50,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-[3-(tert-butyldiphenylsilyloxymethyl)-2,4-dichlorophenyl]-2-cyanopyrrole (820 mg) in anhydrous tetrahydrofuran (16 Ml) was added lithium aluminum hydride (74 mg) and the mixture was stirred at ambient temperature for 1 hour. The reaction mixture was quenched by adding water (2 ml) dropwise under ice-water cooling. Ethyl acetate (50 ml) and water (50 ml) were added thereto and the precipitate was filtered off. The organic layer was isolated and the aqueous layer was extracted with ethyl acetate. The combined organic phases were washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by a silica gel column chromatography eluted with chloroform-methanol to give 2-aminomethyl-1-[3-(tert-butyldiphenylsilyloxymethyl)-2,4-dichlorophenyl]pyrrole (414 mg) as a pale yellow oil.

Aufarbeitung

  1. customThe reaction mixture was quenched
  2. additionby adding water (2 ml) dropwise under ice-water cooling
  3. additionEthyl acetate (50 ml) and water (50 ml) were added
  4. filtrationthe precipitate was filtered off
  5. customThe organic layer was isolated
  6. extractionthe aqueous layer was extracted with ethyl acetate
  7. washThe combined organic phases were washed with brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo
  10. customThe residue was purified by a silica gel column chromatography
  11. washeluted with chloroform-methanol

Quellen und Nachweise

ORD-Eintrag
ord-c6614b0e07a748d289c30a5834b63b27
Quelldatensatz
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06127389

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