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

HRID 661006Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of (±)-5-[1-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-ylsulfanyl)-2-methyl-propyl]-thiophene-2-carboxylic acid ethyl ester (0.458 g, 0.961 mmol) in THF (9.0 mL) is added lithium hydroxide (1N aqueous, 9.0 mL). The mixture is warmed to 70° C. and stirred overnight. The reaction mixture is cooled to rt, acidified with 1N HCl (9.5 mL), extracted into ethyl acetate (3×25 mL), dried over MgSO4, and concentrated to provide (±)-5-[1-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-ylsulfanyl)-2-methyl-propyl]-thiophene-2-carboxylic acid (0.431 g, 96%) as a white foam. MS (ES): 463.2 [M−H]−.

Workup

temperatureThe reaction mixture is cooled to rt
extractionextracted into ethyl acetate (3×25 mL)
dry with materialdried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-b85b3de605f240e0a82d5ce3888a67bc
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084489B2

Reaction notes

Loading…