Dimethyl Sulfoxide → 4-Oxo-4-(4-phenylsulfanyl-phenyl)-butyric acid

HRID 339172Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:14])[CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.[C:15]1([SH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[O:14]=[C:8]([C:5]1[CH:6]=[CH:7][C:2]([S:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:3][CH:4]=1)[CH2:9][CH2:10][C:11]([OH:13])=[O:12]

Participants

Conditions

Temperature: 110 °C

Procedure

4-(4-Fluoro-phenyl)-4-oxo-butyric acid (10.0 g, 51 mmol), thiophenol (5.2 g, 51 mmol), thiophenol (5.2 g, 51 mmol) and powdered potassium carbonate (13.8 g, 100 mmol) were added to 25 mL of dimethyl sulfoxide (DMSO). The reaction mixture was heated to 110° C. for 2 hours, then cooled and diluted by addition of 250 mL water. The aqueous mixture was extracted three times with 100 mL of EtOAc, and the combined organic layers were dried (MgSO4), and evaporated under reduced pressure to yield 11 g (38.5 mmol, 75.5%) of 4-oxo-4-(4-phenylsulfanyl-phenyl)-butyric acid as a crude solid. MS: 287 (M+H)+.

Workup

temperaturecooled
extractionThe aqueous mixture was extracted three times with 100 mL of EtOAc
dry with materialthe combined organic layers were dried (MgSO4)
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-7249f1e7fff049d6b610d9e5928cfd1f
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889906B2

Reaction notes

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