Hydrochloric Acid → HCID 22131683, compound

HRID 1856587Notes

Reaction equation

HRID 1856587 reaction equation
C[O:2][CH2:3][CH:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.[Si](I)(C)(C)C.C(#N)C.Cl>C(Cl)Cl>[OH:2][CH2:3][CH:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:17]=[CH:18][C:19]([O:22][C:23]([F:24])([F:25])[F:26])=[CH:20][CH:21]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 85247Trimethylsilyl iodideHCID 22131714HCID 22131714, compound

Product 1

HCID 22131683HCID 22131683, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4'-(4-methoxymethylcyclohexyl)-4-trifluoromethoxybiphenyl (100 mmol), TMSI (144 mmol), 15 ml of acetonitrile, and 10 ml of methylene chloride was stirred at room temperature for 4 hr. Ice and 6 M HCl were added to the reaction mixture, and the mixture was stirred. The organic phase was washed twice with a saturated aqueous solution of sodium thiosulfate. It was then dried over magnesium sulfate anhydride, and the solvent was distilled off under reduced pressure to give a crude product. The crude product was purified by silica gel column chromatography (eluting solution: toluene--(1:1) mixture of toluene and ethyl acetate) to give 4'-(4-hydroxymethylcyclohexyl)-4-trifluoromethoxybiphenyl (68 mmol, yield 68%).

Workup

  1. stirringthe mixture was stirred
  2. washThe organic phase was washed twice with a saturated aqueous solution of sodium thiosulfate
  3. dry with materialIt was then dried over magnesium sulfate anhydride
  4. distillationthe solvent was distilled off under reduced pressure
  5. customto give a crude product
  6. customThe crude product was purified by silica gel column chromatography (eluting solution: toluene--(1:1) mixture of toluene and ethyl acetate)

Sources & evidence

ORD record
ord-dd2bbc2d0da64a329a6d0097fd8755e8
Source dataset
uspto-grants-2000_11
Patent number
US06143198

Reaction notes

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