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

HRID 35304Notes

Reaction equation

HRID 35304 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 one 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 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 11).

Workup

  1. temperaturerefluxed for one 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 a mixture trichloromethane and methanol (99:1 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated

Sources & evidence

ORD record
ord-67e67dd8dc1c49ee9eca8cd4fd777ddb
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Reaction notes

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