Hydrochloric Acid → HCID 10543697, compound

HRID 2399424Notes

Reaction equation

HRID 2399424 reaction equation
C([O:3][C:4]1(OCC)[CH2:9][CH2:8][C:7]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:13]=2)([CH2:10][F:11])[CH2:6][CH2:5]1)C.Cl>C(OCC)(=O)C>[CH:21]1([O:20][C:14]2[CH:13]=[C:12]([C:7]3([CH2:10][F:11])[CH2:6][CH2:5][C:4](=[O:3])[CH2:9][CH2:8]3)[CH:17]=[CH:16][C:15]=2[O:18][CH3:19])[CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 56620038HCID 56620038, 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 diethyl 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.

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-7e59b3a2ee9f4b7f879c07532680307a
Source dataset
uspto-grants-1995_09
Patent number
US05449686

Reaction notes

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