Water → HCID 22451481, compound

HRID 2185641Notes

Reaction equation

HRID 2185641 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([OH:11])[CH:10]=1)[C:7](=O)[CH2:6][CH:5]2[CH3:13].[Cl-].[Al+3].[Cl-].[Cl-].O>C(OCC)(=O)C>[F:1][C:2]1[CH:10]=[C:9]([OH:11])[C:8]2[CH2:7][CH2:6][CH:5]([CH3:13])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 22451497HCID 22451497, compound

Product 1

HCID 22451481HCID 22451481, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
170 °C

Procedure

5 g of 5-fluoro-2,3-dihydro-7-hydroxy-3-methyl-1H-inden-1-one was heated to 80° C. until all the solid was melted. After adding aluminium chloride (9.3 g) to this melt the reaction mixture was heated to 170° C. during 17 hours. After cooling water and ethyl acetate were added and the mixture was heated on a steam bath until everything was dissolved. The organic layer was separated and washed with water and brine. After removing the solvent the compound was purified by chromatography with the add of heptane/ethylacetate (9:1) resulting in 2.2 g of 6-fluoro-2,3-dihydro-1-methyl-1H-inden-4-ol as a semi-solid, M.S. (C.I.) (M/Z): 167 [M+H]+.

Workup

  1. additionwere added
  2. temperaturethe mixture was heated on a steam bath until everything
  3. dissolutionwas dissolved
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. customAfter removing the solvent the compound
  7. customwas purified by chromatography with the
  8. additionadd of heptane/ethylacetate (9:1)
  9. customresulting in 2.2 g of 6-fluoro-2,3-dihydro-1-methyl-1H-inden-4-ol as a semi-solid

Sources & evidence

ORD record
ord-77230cba025f4ff08ffe977e35957fa0
Source dataset
uspto-grants-2002_06
Patent number
US06403573B1

Reaction notes

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