1-(4-fluorophenyl)-1,3-dihydro-1-[3-(tetrahydro-2H-pyran-2-yloxy)propyl]isobenzofuran → 1-(4-Fluorophenyl)-1,3-dihydroisobenzofuran-1-propanol

HRID 345568Notes

Reaction equation

HRID 345568 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:17][CH2:18][CH2:19][O:20]C3CCCCO3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][O:9]2)=[CH:4][CH:3]=1>Cl.C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:17][CH2:18][CH2:19][OH:20])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][O:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 198835431-(4-fluorophenyl)-1,3-dihydro-1-[3-(tetrahydro-2H-pyran-2-yloxy)propyl]isobenzofuran

Product 1

HCID 198835271-(4-Fluorophenyl)-1,3-dihydroisobenzofuran-1-propanol

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

39.6 Parts of 1-(4-fluorophenyl)-1,3-dihydro-1-[3-(tetrahydro-2H-pyran-2-yloxy)propyl]isobenzofuran were dissolved in 9.8 parts of a hydrochloric acid solution 0.1M and 788 parts of ethanol and the whole was stirred and refluxed for 1 hour. The solvent was evaporated and the residue was taken up in methylbenzene and water. The organic phase was separated, washed with water, dried, filtered and evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (99:1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 24.2 parts of 1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-propanol as a residue (intermediate 94).

Workup

  1. temperaturerefluxed for 1 hour
  2. customThe solvent was evaporated
  3. customThe organic phase was separated
  4. washwashed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column-chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (99:1 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated

Sources & evidence

ORD record
ord-7e531253a8ec4879a6f0d0c7b585807f
Source dataset
uspto-grants-1991_10
Patent number
US05057525

Reaction notes

Loading…