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

Tetrahydrofuran → (4-Ethyl-5-{5-[4-(2-fluorophenoxy)phenyl]-1,2,4-oxadiazol-3-yl}-2-thienyl)methanol

HRID 2247688
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2247688
[Si]([O:8][CH2:9][C:10]1[S:14][C:13]([C:15](=[N:17][OH:18])[NH2:16])=[C:12]([CH2:19][CH3:20])[CH:11]=1)(C(C)(C)C)(C)C.[F:21][C:22]1[CH:37]=[CH:36][CH:35]=[CH:34][C:23]=1[O:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](O)=O)=[CH:27][CH:26]=1.C1(N=C=NC2CCCCC2)CCCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>ClCCl.O.CCCCCC>[CH2:19]([C:12]1[CH:11]=[C:10]([CH2:9][OH:8])[S:14][C:13]=1[C:15]1[N:16]=[C:29]([C:28]2[CH:32]=[CH:33][C:25]([O:24][C:23]3[CH:34]=[CH:35][CH:36]=[CH:37][C:22]=3[F:21])=[CH:26][CH:27]=2)[O:18][N:17]=1)[CH3:20]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 8028TetrahydrofuranHCID 10868DicyclohexylcarbodiimideHCID 2724141Tetrabutylammonium FluorideHCID 200595614-(2-Fluorophenoxy)benzoic acidHCID 725011755-({[t-Butyl(dimethyl)silyl]oxy}methyl)-3-ethyl-N'-hydroxythiophene-2-carboximidamide

Produkt 1

HCID 68521923
(4-Ethyl-5-{5-[4-(2-fluorophenoxy)phenyl]-1,2,4-oxadiazol-3-yl}-2-thienyl)methanol
Ausbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a solution of 5-({[t-butyl(dimethyl)silyl]oxy}methyl)-3-ethyl-N′-hydroxythiophene-2-carboximidamide (0.16 g, 0.50 mmol) that was obtained in Example 10 (10d) and 4-(2-fluorophenoxy)benzoic acid (0.13 g, 0.55 mmol) that was obtained in Example 10 (10e) in dichloromethane (1.5 ml) was added N,N′-dicyclohexylcarbodiimide (0.11 g, 0.55 mmol) with stirring, and the resulting mixture was stirred at room temperature for 30 minutes. After stirring, hexane (2 ml) was added to the reaction mixture, and insoluble materials were removed by filtration, and the filtrate obtained was evaporated in vacuo. Subsequently, to a solution of the residue obtained in tetrahydrofuran (1 ml) was added a 1.0 M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.75 ml, 0.75 mmol) with stirring, and the resulting mixture was stirred at 60° C. for 1 hour. After cooling to room temperature, the reaction mixture was poured into water (10 ml) and extracted with ether. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo, and the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (3:7 to 5:5) as the eluent to afford the title compound (0.18 g) in a yield of 89% as a white crystalline solid.

Aufarbeitung

  1. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  2. stirringAfter stirring
  3. customwere removed by filtration
  4. customthe filtrate obtained
  5. customwas evaporated in vacuo
  6. customSubsequently, to a solution of the residue obtained in tetrahydrofuran (1 ml)
  7. stirringwith stirring
  8. stirringthe resulting mixture was stirred at 60° C. for 1 hour
  9. extractionextracted with ether
  10. washThe extract was washed with a saturated aqueous solution of sodium chloride
  11. dry with materialdried over magnesium sulfate
  12. filtrationAfter filtration
  13. customthe filtrate was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-786e686eeafb41da88f18da9ab72bd9f
Quelldatensatz
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07687491B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion