Triethylamine → 3-Phenylthio-4-(4-(methylsulfonyl)phenyl)-5h-furan-2-one

HRID 1106591Notes

Reaction equation

C(N(CC)CC)C.[S:8]([CH2:15][C:16]([OH:18])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Br[CH2:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1)=O.C1CCN2C(=NCCC2)CC1>C(#N)C>[C:9]1([S:8][C:15]2[C:16](=[O:18])[O:17][CH2:20][C:21]=2[C:23]2[CH:24]=[CH:25][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:27][CH:28]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

At 0° C., triethylamine (335 μL) was added to a solution of thiophenoxyacetic acid (161 mg) and 2-bromo-1-(4-(methylsulfonyl)phenyl) ethanone (272 mg, WO 9500501, example 9, Step 1) in 5 mL of acetonitrile and the mixture was stirred at 0° C. for 1 h. The reaction mixture was then cooled to -20° C. and DBU (265 μL) was added. The mixture was stirred for 30 min. at -20° C. and was quenched by addition of 1N HCl. The product was extracted with EtOAc, dried over sodium sulfate and partially purified by silica gel chromatograph. The impure product was recrystalized from EtOAc/Hexane to afford the title compound as a solid

Workup

temperatureThe reaction mixture was then cooled to -20° C.
stirringThe mixture was stirred for 30 min. at -20° C.
customwas quenched by addition of 1N HCl
extractionThe product was extracted with EtOAc
dry with materialdried over sodium sulfate
custompartially purified by silica gel chromatograph
customThe impure product was recrystalized from EtOAc/Hexane

Sources & evidence

ORD record: ord-70f3ce79dfd2470e9f4600bdcba31dbc
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06057319

Reaction notes

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