Hydrochloric Acid → HCID 10543697, compound

HRID 1780851Notes

Reaction equation

HRID 1780851 reaction equation
C[O:2][C:3]1(OC)[CH2:8][CH2:7][C:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:12]=2)([CH2:9][F:10])[CH2:5][CH2:4]1.Cl>C(OCC)(=O)C>[CH:20]1([O:19][C:13]2[CH:12]=[C:11]([C:6]3([CH2:9][F:10])[CH2:5][CH2:4][C:3](=[O:2])[CH2:8][CH2:7]3)[CH:16]=[CH:15][C:14]=2[O:17][CH3:18])[CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10690272HCID 10690272, compound

Product 1

HCID 10543697HCID 10543697, compoundYield 24.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(fluoromethyl)cyclohexan-1-one dimethyl ketal (0.35 g, 0.95 mmol) in ethyl acetate (2 mL) was treated with 1N hydrochloric acid (2 mL) and the mixture was stirred vigorously and gently heated for 10 min. The mixture was extracted with ethyl acetate, the organic extract was washed with 5% aqueous sodium carbonate, dried (magnesium sulfate) and the solvent was removed in vacuo. Purification by flash chromatography, eluting with 25% ethyl acetate/hexanes, followed by trituration with ether/hexanes, provided a white solid (0.075 g, 24%): m.p. 72°-74 C. Analysis Calc. for C19H25FO3 : C 71.23, H 7.87; found: C 71.22, H 7.70.

Workup

  1. temperaturegently heated for 10 min
  2. extractionThe mixture was extracted with ethyl acetate
  3. extractionthe organic extract
  4. washwas washed with 5% aqueous sodium carbonate
  5. dry with materialdried (magnesium sulfate)
  6. customthe solvent was removed in vacuo
  7. customPurification by flash chromatography
  8. washeluting with 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-632a4855c5b44ce99da073edbb02a799
Source dataset
uspto-grants-1997_05
Patent number
US05631286

Reaction notes

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