Potassium Carbonate → 6-(4-(4-Propylcyclohexyl)phenyl)-3,4-dihydrocoumarin

HRID 2115157

Reaktionsgleichung

Reaktionsgleichung von HRID 2115157
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].Br[C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[O:26][C:25](=[O:30])[CH2:24][CH2:23]2.C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.COCCOC.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>[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([C:20]3[CH:21]=[C:22]4[C:27](=[CH:28][CH:29]=3)[O:26][C:25](=[O:30])[CH2:24][CH2:23]4)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 2667376-Bromochroman-2-oneHCID 31047104-(trans-4-Propylcyclohexyl)phenylboronic Acid

Produkt 1

HCID 586608306-(4-(4-Propylcyclohexyl)phenyl)-3,4-dihydrocoumarinAusbeute 32,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

4-(4-propylcyclohexyl)phenylboronic acid (1.3 g), 6-bromo-3,4-dihydrocoumarin (1.0 g), potassium carbonate (1.2 g), tetrakistriphenylphosphine-palladium (51 mg), and tetrabutylammonium bromide (10 mg) were suspended in DME (10 ml), and the suspension was stirred under reflux by heating for 3 hours. After completion of the reaction, the reaction mixture was added in ice water and extracted with toluene. An organic layer was washed with water and then dried over anhydrous magnesium sulfate. The solution was concentrated in vacuo and then subjected to isolation and purification by silica gel column chromatography, thereby obtaining a titled compound (500 mg). As a result of a variety of instrumental analyses, it was confirmed that this was the titled compound.

Aufarbeitung

  1. temperatureunder reflux
  2. temperatureby heating for 3 hours
  3. customAfter completion of the reaction
  4. extractionextracted with toluene
  5. washAn organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe solution was concentrated in vacuo
  8. customsubjected to isolation and purification by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c6aa1151a63a4378ad172fa609fefd4c
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07435455B2

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