Diethyl Ether → 4-Hydroxy-2-methylene-1-indanone

HRID 974778Notes

Reaction equation

HRID 974778 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].O1COCO[CH2:13]1.FC(F)(F)C([O-])=O.C[NH2+]C1C=CC=CC=1.CCOCC>C1COCC1>[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][C:5](=[CH2:13])[C:6]2=[O:11]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 80811,3,5-TrioxaneHCID 5905474-Hydroxy-1-indanoneHCID 2724109N-Methylanilinium trifluoroacetate

Product 1

HCID 199694214-Hydroxy-2-methylene-1-indanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-hydroxy-1-indanone (1 g; 6.7 mmol) in THF were added, at ambient temperature and under argon, powdered 1,3,5-trioxane (1.2 g; 13.4 mmol) and N-methyl-N-phenylammonium trifluoroacetate (2.9 g; 13.4 mmol). The suspension was refluxed for 4 hours. Ether was added to the mixture and the resulting precipitate was filtered off. The organic phase was washed with water, dried over MgSO4, filtered and evaporated. The residue obtained was purified by flash chromatography on silica gel, eluting with petroleum ether/ethyl acetate (8/2) to give 4-hydroxy-2-methylene-1-indanone as a beige solid (0.76 g; 70%).

Workup

  1. temperatureThe suspension was refluxed for 4 hours
  2. filtrationthe resulting precipitate was filtered off
  3. washThe organic phase was washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue obtained
  8. customwas purified by flash chromatography on silica gel
  9. washeluting with petroleum ether/ethyl acetate (8/2)

Sources & evidence

ORD record
ord-26716f3e1d7d404f9cb3a1d1871c80d6
Source dataset
uspto-grants-1997_03
Patent number
US05607928

Reaction notes

Loading…