Water → 2'-methyl-4'-(tetrahydro-2H-pyran-2-yloxy)biphenyl-3-carbaldehyde

HRID 273368Notes

Reaction equation

HRID 273368 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:5]([O:6][CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][O:8]2)=[CH:4][C:3]=1[CH3:15].[CH:16]([C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1)=[O:17].O.C(OCC)(=O)C>C(=O)([O-])[O-].[Na+].[Na+].C(O)C.C1(C)C=CC=CC=1.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>[CH3:15][C:3]1[CH:4]=[C:5]([O:6][CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][O:8]2)[CH:13]=[CH:14][C:2]=1[C:22]1[CH:21]=[CH:20][CH:19]=[C:18]([CH:16]=[O:17])[CH:23]=1

Participants

9

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 27343563-Formylphenylboronic acidHCID 231118382-(4-bromo-3-methylphenoxy)tetrahydro-2H-pyran

Product 1

HCID 231118322'-methyl-4'-(tetrahydro-2H-pyran-2-yloxy)biphenyl-3-carbaldehydeYield 82.5%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
80 °C

Procedure

2-(4-Bromo-3-methylphenoxy)tetrahydro-2H-pyran (7.11 g, 25.2 mmol, including 3,4-dihydro-2H-pyran) and (3-formylphenyl)boronic acid (4.50 g, 30.0 mmol) were dissolved in a mixture of 1 M aqueous sodium carbonate solution (60 mL), ethanol (30 mL) and toluene (60 mL), and after argon substitution, tetrakis(triphenylphosphine)palladium(0) (1.73 g, 1.50 mmol) was added. The reaction mixture was stirred under an argon atmosphere at 80° C. for 15 hrs. The reaction mixture was cooled, water and ethyl acetate were added, and insoluble material was filtered off through celite. The organic layer of the filtrate was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5%-30% ethyl acetate/hexane) to give the title compound (6.16 g, yield 82%, 2 steps) as a pale-yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationinsoluble material was filtered off through celite
  3. washThe organic layer of the filtrate was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (5%-30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4d1f54cbebde4d5eaa283b315695a693
Source dataset
uspto-grants-2008_11
Patent number
US07456218B2

Reaction notes

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