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

HRID 2115157Notes

Reaction equation

HRID 2115157 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

HCID 586608306-(4-(4-Propylcyclohexyl)phenyl)-3,4-dihydrocoumarinYield 32.6%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c6aa1151a63a4378ad172fa609fefd4c
Source dataset
uspto-grants-2008_10
Patent number
US07435455B2

Reaction notes

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