Tetrahydrofuran → 4-[Cyclohexyl(5-cyclohexyl-2-ethylthiophen-3-yl)methoxy]benzoic acid

HRID 1877005Notes

Reaction equation

HRID 1877005 reaction equation
[CH:1]1([CH:7]([C:19]2[CH:23]=[C:22]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[S:21][C:20]=2[CH2:30][CH3:31])[O:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O1CCCC1.[OH-].[Na+]>C(O)C>[CH:1]1([CH:7]([C:19]2[CH:23]=[C:22]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[S:21][C:20]=2[CH2:30][CH3:31])[O:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:17][CH:18]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68515167Methyl 4-[cyclohexyl(5-cyclohexyl-2-ethylthiophen-3-yl)methoxy]benzoate

Product 1

HCID 685124004-[Cyclohexyl(5-cyclohexyl-2-ethylthiophen-3-yl)methoxy]benzoic acidYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of methyl 4-[cyclohexyl(5-cyclohexyl-2-ethylthiophen-3-yl)methoxy]benzoate (560 mg) synthesized above, tetrahydrofuran (10 mL) and ethanol (10 mL) was added 1N aqueous sodium hydroxide solution (5 mL), and the mixture was stirred with heating under reflux overnight. The reaction mixture was concentrated under reduced pressure, 1N hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give a white solid. The obtained solid was recrystallized from ethyl acetate-hexane to give the title compound (194 mg, 36%) as a colorless crystal.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure, 1N hydrochloric acid
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto give a white solid
  10. customThe obtained solid was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-d979581e3f054b2abe41db42b66e6fd1
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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