Ethanol → HCID 23082902, compound

HRID 2422297Notes

Reaction equation

HRID 2422297 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:9][CH:8]=1.[CH:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O)=[O:26].C(=O)([O-])[O-].[K+].[K+].C(O)C>C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:2]1[CH:24]=[CH:23][CH:22]=[C:4]([CH2:5][O:6][C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:9][CH:8]=2)[CH:3]=1)=[O:26]

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 2921892-Formylphenylboronic acidHCID 67146001HCID 67146001, compound

Product 1

HCID 23082902HCID 23082902, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of tert-butyl 3-[4-[(3-bromobenzyl)oxy]phenyl]propanoate (3.5 g, 8.94 mmol), 2-formylphenylboronic acid (1.47 g, 9.83 mmol), tetrakistriphenylphosphine palladium (413 mg, 0.36 mmol), 2N potassium carbonate aqueous solution (7 mL), ethanol (7 mL) and toluene (70 mL) was stirred under an argon atmosphere at 80° C. for 14 hrs. The reaction mixture was cooled, diluted with ethyl acetate, washed with water, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-4/1) to give the title compound (3.62 g, 97%) as a colorless oil.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-4/1)

Sources & evidence

ORD record
ord-28ea9ea2b35b42f78accd8174d6a21ad
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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