Diazomethane → HCID 67289140, compound

HRID 62918Notes

Reaction equation

HRID 62918 reaction equation
[CH2:1]([O:3][C:4](=[O:16])/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[F:15])[CH3:2].[N+](=[CH2:19])=[N-]>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:3][C:4]([CH:5]1[CH2:19][CH:6]1[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[F:15])=[O:16])[CH3:2]

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 59838333ethyl(2E)-3-(2-fluoro-4-methoxyphenyl)acrylate

Product 1

HCID 67289140HCID 67289140, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(E)-3-(2-Fluoro-4-methoxy-phenyl)-acrylic acid ethyl ester (0.3 g, 1.34 mmol) obtained in Step A was dissolved in THF (10 mL), and diazomethane solution (21.4 mL, 5.36 mmol, 0.25M ether) was added thereto. After the reactant was cooled to 0˜5° C., palladium(II) acetate (45 mg, 0.2 mmol) was added slowly thereto, and the mixture was stirred at room temperature for 5 hours. After the termination of the reaction, the reactant was filtered by using celite, concentrated under reduced pressure, and purified by column chromatography (eluent, EtOAc/Hex=1/10) to obtain the title compound (0.16 g, 51%).

Workup

  1. temperatureAfter the reactant was cooled to 0˜5° C.
  2. customAfter the termination of the reaction
  3. filtrationthe reactant was filtered
  4. concentrationconcentrated under reduced pressure
  5. custompurified by column chromatography (eluent, EtOAc/Hex=1/10)

Sources & evidence

ORD record
ord-3044348e5fa645ae9c52c0db2751fc16
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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