Hydrochloric Acid → HCID 67484499, compound

HRID 660990Notes

Reaction equation

HRID 660990 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:10]2([CH2:15][O:16][C:17]3[CH:22]=[C:21]([CH3:23])[C:20]([C:24]4[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=4)=[C:19]([CH3:34])[CH:18]=3)[CH2:14][CH:13]=[CH:12][CH2:11]2)=[CH:8][CH:9]=1)=[O:4].[Li+].[OH-].Cl>C1COCC1>[CH3:34][C:19]1[CH:18]=[C:17]([O:16][CH2:15][C:10]2([C:7]3[S:6][C:5]([C:3]([OH:4])=[O:2])=[CH:9][CH:8]=3)[CH2:11][CH:12]=[CH:13][CH2:14]2)[CH:22]=[C:21]([CH3:23])[C:20]=1[C:24]1[CH:25]=[CH:26][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67484581HCID 67484581, compound

Product 1

HCID 67484499HCID 67484499, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 5-[1-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yloxymethyl)-cyclopent-3-enyl]-thiophene-2-carboxylic acid methyl ester (0.239 g, 0.492 mmol) in THF (5.0 mL) is treated with LiOH (1N aqueous, 5.0 mL, 5.0 mmol), warmed to 70° C., and stirred overnight. The reaction mixture is cooled to rt, acidified with HCl (1N aqueous, 5.2 mL), and extracted with EtOAc (3×10 mL). The combined extracts are dried over MgSO4, filtered, and concentrated to provide 5-[1-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yloxymethyl)-cyclopent-3-enyl]-thiophene-2-carboxylic acid (0.210 g, 90%) as a yellow foam. MS (ES): 471.2 [M−H]−.

Workup

  1. temperatureThe reaction mixture is cooled to rt
  2. extractionextracted with EtOAc (3×10 mL)
  3. dry with materialThe combined extracts are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e66ac56c02e54115b6079abe106249dc
Source dataset
uspto-grants-2011_12
Patent number
US08084489B2

Reaction notes

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