Water → HCID 23159922, compound

HRID 2422219Notes

Reaction equation

HRID 2422219 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[Sn](C)(C)C.O>CN(C)C=O>[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:2]1[CH:3]=[C:4]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11021057Pyridine, 2-(trimethylstannyl)-HCID 23136270Methyl 4-[(3-bromophenyl)methoxy]benzenepropanoate

Product 1

HCID 23159922HCID 23159922, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 4-[(3-bromophenyl)methoxy]benzenepropanoate (0.70 g, 2.0 mmol) and 2-pyridyltrimethyltin (0.60 g, 2.4 mmol) were dissolved in N,N-dimethylformamide (15 mL) and, after argon substitution, dichlorobistriphenylphosphinepalladium (II) (0.10 g, 0.070 mmol) was added. The reaction mixture was heated under reflux overnight under an argon atmosphere. The reaction mixture was cooled, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5:1) to give the title compound (0.24 g, yield 35%) as a colorless oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux overnight under an argon atmosphere
  3. temperatureThe reaction mixture was cooled
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5:1)

Sources & evidence

ORD record
ord-5917cc0c015741419c3d273b73b4330b
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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