Oxygen → 4-Phenoxy-2,3-dihydro-1H-inden-1-one

HRID 445117Notes

Reaction equation

HRID 445117 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH2:13][CH2:14][C:15]2=[O:20].C(Cl)Cl.O=O>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(N(CC)CC)C>[O:10]([C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH2:13][CH2:14][C:15]2=[O:20])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 977OxygenHCID 6344DichloromethaneHCID 66827Phenylboronic AcidHCID 5905474-Hydroxy-1-indanone

Product 1

HCID 124391004-Phenoxy-2,3-dihydro-1H-inden-1-oneYield 72.7%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 8471TriethylamineSolvent

Procedure

To phenyl boronic acid (1.0 g) and 4-hydroxy-2,3-dihydro-1H-inden-1-one (1.0 g), methylene chloride (67 mL) was added and thereto, copper (II) acetate (1.4 g), molecular sieves 4A (1.9 g), and triethylamine (4.7 mL) were added, followed by stirring the resultant reaction mixture at room temperature in an oxygen atmosphere for 19 hours. The reaction mixture was filtered through a pad of Celite and the filtered substance was washed with ethyl acetate. To the resultant filtrate, a 1M aqueous solution of sodium hydroxide was added and the resultant mixture was filtered through a pad of Celite again. The resultant filtrate was phase-separated into an aqueous phase and an organic phase and the aqueous phase was extracted with ethyl acetate to combine the resultant organic phase with the above organic phase. The combined organic phase was washed with saturated saline and was dried over sodium sulfate anhydride. From the organic phase, the solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography to obtain the subject compound (1.1 g) as an orange solid.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. washthe filtered substance was washed with ethyl acetate
  3. additionTo the resultant filtrate, a 1M aqueous solution of sodium hydroxide was added
  4. filtrationthe resultant mixture was filtered through a pad of Celite again
  5. customThe resultant filtrate was phase-separated into an aqueous phase
  6. extractionan organic phase and the aqueous phase was extracted with ethyl acetate
  7. washThe combined organic phase was washed with saturated saline
  8. dry with materialwas dried over sodium sulfate anhydride
  9. distillationFrom the organic phase, the solvent was distilled off under reduced pressure
  10. customthe resultant residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-eab8db1562764a7fa2d623c218a0a024
Source dataset
uspto-grants-2013_07
Patent number
US08476287B2

Reaction notes

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