Hydrochloric Acid → (+/-)-5-[1-(2,6-Dimethyl-4'-trifluoromethyl-biphenyl-4-yloxy)-ethyl]-thiophene-2-carboxylic acid

HRID 660982Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of (±)-5-[1-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yloxy)-ethyl]-thiophene-2-carboxylic acid ethyl ester (0.636 g, 1.42 mmol) in THF (14 mL) is added lithium hydroxide (1N aqueous, 14 mL). The mixture is warmed to 70° C. and stirred overnight. The reaction mixture is acidified with 1N HCl (15 mL), extracted into ethyl acetate (3×25 mL), dried over MgSO4, and concentrated, to provide (±)-5-[1-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yloxy)-ethyl]-thiophene-2-carboxylic acid (0.552 g, 92%) as a white foam. MS (ES): 419.2 [M−H]−.

Workup

extractionextracted into ethyl acetate (3×25 mL)
dry with materialdried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-2bb39986a0aa43d6838c330d4b6ea79f
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084489B2

Reaction notes

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