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Potassium Carbonate → 2-(4-chlorophenyl)-5,5-dimethyl-1-Cyclohexene-1-carboxaldehyde

HRID 2406233
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2406233
Br[C:2]1[CH2:7][CH2:6][C:5]([CH3:9])([CH3:8])[CH2:4][C:3]=1[CH:10]=[O:11].[Cl:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]2[CH2:7][CH2:6][C:5]([CH3:9])([CH3:8])[CH2:4][C:3]=2[CH:10]=[O:11])=[CH:15][CH:14]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 251391912-Bromo-5,5-dimethylcyclohex-1-enecarbaldehyde

Produkt 1

HCID 445943302-(4-chlorophenyl)-5,5-dimethyl-1-Cyclohexene-1-carboxaldehydeAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 962WaterLösungsmittel
HCID 6344DichloromethaneLösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A suspension of 2-bromo-5,5-dimethylcyclohex-1-enecarbaldehyde (250 mg, 1.15 mmol), 4-chlorophenyl boronic acid (270 mg, 1.727 mmol) and Pd(Ph3P)4 (66.5 mg, 0.058 mmol) in dioxane (2.5 mL) was stirred at room temperature in a 5 mL microwave vial under an atmosphere of nitrogen. A solution of potassium carbonate (318 mg, 2.3 mmol) in water (0.3 mL) was added and the solution became clear. The vial was capped and heated to 100° C. for 12 minutes in a microwave. The reaction was cooled to room temperature, diluted with CH2Cl2, filtered through a plug of Celite, and concentrated. The crude residue was purified by flash chromatography on silica gel (0-25% EtOAc/heptanes) to afford 2-(4-chlorophenyl)-5,5-dimethylcyclohex-1-enecarbaldehyde as a clear colorless oil (220 mg, 77% yield).

Aufarbeitung

  1. customThe vial was capped
  2. temperatureheated to 100° C. for 12 minutes in a microwave
  3. temperatureThe reaction was cooled to room temperature
  4. filtrationfiltered through a plug of Celite
  5. concentrationconcentrated
  6. customThe crude residue was purified by flash chromatography on silica gel (0-25% EtOAc/heptanes)

Quellen und Nachweise

ORD-Eintrag
ord-98f82e3de3a041c3b2a671f904599cb3
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08809352B2

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