Hydrochloric Acid → HCID 10543697, compound

HRID 2394505Notes

Reaction equation

HRID 2394505 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.C1(OC2C=C(C3(CF)CCC(=O)CC3)C=CC=2OC)CCCC1.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 131720838HCID 131720838, 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 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.

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-38094ac2d3e04e8da1bd1dbf6ae91d32
Source dataset
uspto-grants-1998_09
Patent number
US05811455

Reaction notes

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