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

Ethanol → 1-[5-(1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)pyridin-2-yl]-5-[4-(cyclopropylsulfonyl)phenyl]-2-methyl-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

HRID 1881849
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1881849
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21](=[O:25])[CH:22]=[CH:23][CH3:24])[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C(O)C.O1CCCC1.[Si:34]([O:41][CH:42]([C:44]1[CH:45]=[CH:46][C:47]([CH:50]=[O:51])=[N:48][CH:49]=1)[CH3:43])([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35]>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(OCC)(=O)C.C(N(CC)CC)C>[Si:34]([O:41][CH:42]([C:44]1[CH:45]=[CH:46][C:47]([C:50](=[O:51])[CH:23]([CH3:24])[CH2:22][C:21](=[O:25])[CH:13]([C:10]2[CH:9]=[CH:8][C:7]([S:4]([CH:1]3[CH2:2][CH2:3]3)(=[O:6])=[O:5])=[CH:12][CH:11]=2)[CH2:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[N:48][CH:49]=1)[CH3:43])([C:37]([CH3:40])([CH3:38])[CH3:39])([CH3:36])[CH3:35]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 593313475-(1-{[Tert-butyl(dimethyl)silyl]oxy}ethyl)pyridine-2-carbaldehydeHCID 684311882-[4-(cyclopropylsulfonyl)phenyl]-1-(tetrahydro-2H-pyran-4-yl)hex-4-en-3-one

Produkt 1

HCID 593312241-[5-(1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)pyridin-2-yl]-5-[4-(cyclopropylsulfonyl)phenyl]-2-methyl-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione
Ausbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chlorideKatalysatorHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-[4-(cyclopropylsulfonyl)phenyl]-1-(tetrahydro-2H-pyran-4-yl)hex-4-en-3-one (180 mg) in a mixed solvent of ethanol (3 mL) and tetrahydrofuran (3 mL) were added 5-(1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)pyridine-2-carbaldehyde (158 mg), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (14.7 mg) and triethylamine (29.9 μL), and the mixture was stirred with heating under reflux under argon atmosphere for 3 hr. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (180 mg, yield 58%) was obtained as a pale-yellow oil from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). MS: 628 (MH+).

Aufarbeitung

  1. temperaturewith heating
  2. temperatureunder reflux under argon atmosphere for 3 hr
  3. washwashed with water
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c8166407cc3a449d8d3270a8738e4e25
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08318746B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion