StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Dimethyl Sulfoxide → Methyl 1-allyl-3-cyclohexyl-2-(2-formylphenyl)-1H-indole-6-carboxylate

HRID 1518257
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1518257
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23]([O:25][CH3:26])=[O:24])[CH:21]=2)[C:16]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[C:15]1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH2:39][OH:40])[CH:12]=[CH2:13].CCN(CC)CC>C(Cl)Cl>[CH2:11]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23]([O:25][CH3:26])=[O:24])[CH:21]=2)[C:16]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[C:15]1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH:39]=[O:40])[CH:12]=[CH2:13]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 68702775Methyl 1-allyl-3-cyclohexyl-2-[2-(hydroxymethyl)phenyl]-1H-indole-6-carboxylate

Produkt 1

HCID 86637858Methyl 1-allyl-3-cyclohexyl-2-(2-formylphenyl)-1H-indole-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
3×

Versuchsvorschrift

Oxalyl chloride (2.5 eq., 2M solution in DCM) was added at −70° C. under nitrogen atmosphere to a solution of DMSO (5 eq.) in anhydrous DCM and the mixture was stirred for 30 min; a solution of methyl 1-allyl-3-cyclohexyl-2-[2-(hydroxymethyl)phenyl]-1H-indole-6-carboxylate in DCM was then added and stirring was continued at the same temperature for 30 min. before NEt3 (8 eq.) was added. After stirring for 20 min. at 0° C. the mixture was diluted with DCM, then washed with water, 1N HCl, saturated aq. NaHCO3 solution and brine. The organic phase was dried over Na2SO4 and evaporated in vacuo. The residual material was used in the next step without purification. MS (ES+): 402.2 (M+H+).

Aufarbeitung

  1. stirringstirring
  2. additionwas added
  3. stirringAfter stirring for 20 min. at 0° C. the mixture
  4. washwashed with water, 1N HCl, saturated aq. NaHCO3 solution and brine
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customevaporated in vacuo
  7. customThe residual material was used in the next step without purification

Quellen und Nachweise

ORD-Eintrag
ord-1763e5c80cc94d4d83d1e3aa9dc0335c
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08232390B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion