Tetrabutylammonium Fluoride → 1-(2,4-Dichloro-3-hydroxymethylphenyl)2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole

HRID 365576Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 365576
[Si]([O:18][CH2:19][C:20]1[C:21]([Cl:48])=[C:22]([N:27]2[CH:31]=[CH:30][CH:29]=[C:28]2[CH2:32][NH:33][C:34](=[O:47])[CH:35]=[CH:36][C:37]2[CH:42]=[CH:41][C:40]([C:43](=[O:46])[NH:44][CH3:45])=[CH:39][CH:38]=2)[CH:23]=[CH:24][C:25]=1[Cl:26])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:48][C:21]1[C:20]([CH2:19][OH:18])=[C:25]([Cl:26])[CH:24]=[CH:23][C:22]=1[N:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[CH2:32][NH:33][C:34](=[O:47])[CH:35]=[CH:36][C:37]1[CH:38]=[CH:39][C:40]([C:43](=[O:46])[NH:44][CH3:45])=[CH:41][CH:42]=1

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 542764421-[3-(Tert-butyldiphenylsilyloxymethyl)-2,4-dichlorophenyl]-2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole

Produkt 1

HCID 539366561-(2,4-Dichloro-3-hydroxymethylphenyl)2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrroleAusbeute 48,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 1-[3-(tert-butyldiphenylsilyloxymethyl)-2,4-dichlorophenyl]-2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole (620 mg) in tetrahydrofuran (6 ml) was added 1N solution of tetrabutylammonium fluoride in tetrahydrofuran (2.5 ml). The mixture was stirred at ambient temperature for 6 hours and partitioned between ethyl acetate and water. The organic layer was isolated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with 1N hydrochloric acid and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with methanol to give 1-(2,4-dichloro-3-hydroxymethylphenyl)-2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole (197 mg) as a brownish powder.

Aufarbeitung

  1. custompartitioned between ethyl acetate and water
  2. customThe organic layer was isolated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with 1N hydrochloric acid and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was triturated with methanol

Quellen und Nachweise

ORD-Eintrag
ord-bddccdec49544842b767e860de4630b0
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06127389

Notizen zur Reaktion

Wird geladen…