Hydrochloric Acid → HCID 54335673, compound

HRID 1741844Notes

Reaction equation

HRID 1741844 reaction equation
[C:1]([O:4][CH:5]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]([O:20]COC)[CH2:16][CH2:17][CH2:18][CH3:19])=[C:11]([F:24])[CH:10]=1)[CH:6]([CH3:8])[CH3:7])(=[O:3])[CH3:2].Cl>C(O)(=O)C>[C:1]([O:4][CH:5]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:20])[CH2:16][CH2:17][CH2:18][CH3:19])=[C:11]([F:24])[CH:10]=1)[CH:6]([CH3:7])[CH3:8])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53791239HCID 53791239, compound

Product 1

HCID 54335673HCID 54335673, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-[3-fluoro-4-[1-(methoxymethoxy)pentyl]phenyl]-2-methylpropyl acetate (110 mg) and 1N hydrochloric acid (0.3 ml) in acetic acid (3 ml) was stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure, and the residue was dissolved in ethyl acetate. The organic solution was washed with aqueous sodium bicarbonate, water and brine, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel column eluting with a mixture of hexane and ethyl acetate to give 1-[3-fluoro-4-(1-hydroxypentyl)phenyl]-2-methylpropyl acetate (70 mg) as an oil.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe organic solution was washed with aqueous sodium bicarbonate, water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel column
  7. washeluting with a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-803e7bf50bb746bfb143f53614f12890
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

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