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

Sodium Hydroxide → HCID 21110471, Verbindung

HRID 1766935
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1766935
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=2)[CH2:4][O:3]1.[OH-:13].[Na+].[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Cl)=[CH:19][CH:18]=1.Cl[C:26]([O:28][CH2:29][CH:30]=[CH2:31])=[O:27]>O1CCCC1CO.CN(C1C=CN=CC=1)C.C(OCC)(=O)C.CCCCCC.ClCCl>[CH2:29]([O:28][C:26]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]#[N:12])=[CH:9][C:10]=1[C:2]([O:1][CH2:21][C:20]1[CH:23]=[CH:24][C:17]([O:16][CH3:15])=[CH:18][CH:19]=1)=[O:13])=[O:27])[CH:30]=[CH2:31]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 4

HCID 14798Sodium HydroxideHCID 18052Allyl chloroformateHCID 699934-Methyloxybenzyl chlorideHCID 132895623-Oxo-1,3-dihydroisobenzofuran-5-carbonitrile

Produkt 1

HCID 21110471HCID 21110471, VerbindungAusbeute 46,9 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 14284
4-(Dimethylamino)pyridine
Katalysator
HCID 6344DichloromethaneLösungsmittel
HCID 7360Tetrahydrofurfuryl alcoholLösungsmittel
HCID 8058HexaneLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

1-Oxo-1,3-dihydroisobenzofuran-6-carbonitrile (3.01 g, 18.9 mmol) obtained from Example 5-(2) was dissolved in a mixed solvent (200 ml) of tetrahydrofuran-methanol (3:1), and an aqueous solution of sodium hydroxide (1.004N; 17.4 ml, 17.4 mmol) was added thereto over a period of 10 minutes. The mixture was stirred at room temperature for 30 minutes, and the solvent was distilled off under reduced pressure. The resulting residue was dried using a vacuum pump. The obtained solid was dissolved in N,N-dimethylformamide (40 ml), and 4-methoxybenzyl chloride (2.96 g, 18.9 mmol) was added thereto. The mixture was heated at 70-80° C. for 1 hour. After cooling the mixture to 0° C., dichloromethane (40 ml) was added thereto, and 4-(N,N-dimethylamino)pyridine (5.78 g, 47.3 mmol) and allyl chloroformate (4.56 g, 37.9 mmol) were added thereto, then the mixture was stirred at the same temperature for 30 minutes. The mixture was diluted with ethyl acetate and then washed successively with water and an aqueous solution of sodium chloride. The resulting mixture was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to give an oily residue. The residue was subjected to chromatography on a silica gel (100 g) column (eluent; hexane:ethyl acetate=3:1) to afford the title compound (3.11 g, 43% yield) as a colorless oil.

Aufarbeitung

  1. distillationthe solvent was distilled off under reduced pressure
  2. customThe resulting residue was dried
  3. dissolutionThe obtained solid was dissolved in N,N-dimethylformamide (40 ml)
  4. temperatureThe mixture was heated at 70-80° C. for 1 hour
  5. temperatureAfter cooling the mixture to 0° C.
  6. stirringthe mixture was stirred at the same temperature for 30 minutes
  7. washwashed successively with water
  8. dry with materialThe resulting mixture was dried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customto give an oily residue

Quellen und Nachweise

ORD-Eintrag
ord-18b7f0ef30864a6999f2889420e83ed1
Quelldatensatz
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07230023B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion