Ethylene Glycol → HCID 21951285, compound

HRID 2215614Notes

Reaction equation

HRID 2215614 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([CH3:13])=[C:6]2[C:10]=1[C:9](=[O:11])[CH:8]([CH3:12])[CH2:7]2.[C:14]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].C(=O)([O-])[O-].[Na+].[Na+].C(O)CO>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=C(S([O-])(=O)=O)C=C(P(C2C=CC=C(S([O-])(=O)=O)C=2)C2C=CC=C(S([O-])(=O)=O)C=2)C=1.[Na+].[Na+].[Na+]>[CH3:12][CH:8]1[CH2:7][C:6]2[C:10](=[C:2]([C:21]3[CH:22]=[CH:23][C:18]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:19][CH:20]=3)[CH:3]=[CH:4][C:5]=2[CH3:13])[C:9]1=[O:11]

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 10340Sodium CarbonateHCID 27343204-tert-Butylphenylboronic acidHCID 21951268HCID 21951268, compound

Product 1

HCID 21951285HCID 21951285, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6099338Trisodium 3,3',3''-phosphinetriyltris(benzene-1-sulphonate)CatalystHCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

13.4 (68.8 mmol) of 7-chloro-2,4-dimethyl-1-indanone (1c), 14.71 g (82.6 mmol) of 4-tert-butylphenylboronic acid, 16.05 g (151 mmol) of sodium carbonate, 188 ml of ethylene glycol and 30.7 ml of water were placed under a protective gas atmosphere in a reaction vessel and heated to 80° C. While stirring vigorously, a freshly prepared catalyst solution of 77 mg (0.343 mmol) of palladium acetate, 1.7 ml (1.01 mmol) of an aqueous TPPTS solution (0.6 molar) in 25 ml of water was added to the reaction components and the reaction mixture was refluxed for 3 hours until the reaction was complete. After cooling to room temperature, the ethylene glycol phase was extracted three times with a total of 900 ml of toluene. The combined toluene phases were washed twice with a total of 250 ml of sodium chloride solution and dried over 150 g of sodium sulfate. Removal of the solvent, drying of the residue and subsequent distillation in an oil pump vacuum gave 18.59 g of (1d).

Workup

  1. temperaturethe reaction mixture was refluxed for 3 hours until the reaction
  2. temperatureAfter cooling to room temperature
  3. extractionthe ethylene glycol phase was extracted three times with a total of 900 ml of toluene
  4. washThe combined toluene phases were washed twice with a total of 250 ml of sodium chloride solution
  5. dry with materialdried over 150 g of sodium sulfate
  6. customRemoval of the solvent
  7. customdrying of the residue and subsequent distillation in an oil pump vacuum

Sources & evidence

ORD record
ord-c2976c4f88774d70be921d01bf0e1134
Source dataset
uspto-grants-2006_09
Patent number
US07109278B2

Reaction notes

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