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Ammonium Chloride → 5-Cyclohex-1-en-1-yl-7-isopropyl-2,2-dimethyl-4-oxochroman-6-carbaldehyde

HRID 1516704
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1516704
FC(F)(F)S(O[C:7]1[C:16]([CH:17]=[O:18])=[C:15]([CH:19]([CH3:21])[CH3:20])[CH:14]=[C:13]2[C:8]=1[C:9](=[O:24])[CH2:10][C:11]([CH3:23])([CH3:22])[O:12]2)(=O)=O.[C:27]1(B(O)O)[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl-].[NH4+]>O1CCOCC1.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>[C:27]1([C:7]2[C:16]([CH:17]=[O:18])=[C:15]([CH:19]([CH3:21])[CH3:20])[CH:14]=[C:13]3[C:8]=2[C:9](=[O:24])[CH2:10][C:11]([CH3:22])([CH3:23])[O:12]3)[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 38629021-Cyclohexenylboronic acidHCID 580029926-Formyl-7-isopropyl-2,2-dimethyl-4-oxo-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate

Produkt 1

HCID 580029485-Cyclohex-1-en-1-yl-7-isopropyl-2,2-dimethyl-4-oxochroman-6-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 365 mg (930 μmol) of 6-formyl-7-isopropyl-2,2-dimethyl-4-oxo-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate (Example 19A), 152 mg (1.20 mmol) of cyclohex-1-en-1-ylboronic acid, 75 mg (60 μmol) of tetrakis(triphenylphosphine)palladium and 334 mg (1.57 mmol) of potassium phosphate in 5.5 ml of degassed dioxane is stirred at 100° C. overnight. After cooling to room temperature, ammonium chloride solution is added and the mixture is extracted twice with ethyl acetate. The combined organic phases are dried over sodium sulfate, the solvent is then removed under reduced pressure and the residue is purified by column chromatography on silica gel (mobile phase:cyclohexane/ethyl acetate 20:1).

Aufarbeitung

  1. extractionthe mixture is extracted twice with ethyl acetate
  2. dry with materialThe combined organic phases are dried over sodium sulfate
  3. customthe solvent is then removed under reduced pressure
  4. customthe residue is purified by column chromatography on silica gel (mobile phase:cyclohexane/ethyl acetate 20:1)

Quellen und Nachweise

ORD-Eintrag
ord-7134e116541c44c5b336197b8cbb6ebe
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08227511B2

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