Diazomethane → 6-Cyclopropyl-5-(2-hydroxyethyl)-2-benzofuran-1(3H)-one

HRID 1474339Notes

Reaction equation

HRID 1474339 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:13]([CH:14]=[CH2:15])=[CH:12][C:7]2[C:8](=[O:11])[O:9][CH2:10][C:6]=2[CH:5]=1.[N+](=[CH2:18])=[N-]>C(OCC)C.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH:14]1([C:13]2[C:4]([CH2:3][CH2:2][OH:1])=[CH:5][C:6]3[CH2:10][O:9][C:8](=[O:11])[C:7]=3[CH:12]=2)[CH2:18][CH2:15]1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 666438955-(2-Hydroxyethyl)-6-vinyl-2-benzofuran-1(3H)-one

Product 1

HCID 666466836-Cyclopropyl-5-(2-hydroxyethyl)-2-benzofuran-1(3H)-one

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a 100 ml flask containing a stir bar was added 5-(2-Hydroxyethyl)-6-vinyl-2-benzofuran-1(3H)-one (0.9 g, 4.41 mmol), and Palladium diacetate (0.049 g, 0.220 mmol), followed by addition of a freshly prepared diazomethane (3.7 g, 88 mmol) in diethyl ether (10 mL) over a course of 20 minutes. The resulting mixture was then stirred at room temperature in a shielded environment for 1 h. When the reaction was complete, the solvent was concentrated to dryness, dissolved in EtOAc, and washed with brine, dried (Na2SO4), filtered and concentrated to dryness. The resulting residue was used for the next step without further purification.

Workup

  1. additionTo a 100 ml flask containing a stir bar
  2. concentrationthe solvent was concentrated to dryness
  3. dissolutiondissolved in EtOAc
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe resulting residue was used for the next step without further purification

Sources & evidence

ORD record
ord-d81c732df36c45c5939ea399475b7c3c
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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