Thiophenol → 4-(Phenylsulfanyl)but-3-en-2-one

HRID 1004492Notes

Reaction equation

CO/[CH:3]=[CH:4]/[C:5](=[O:7])[CH3:6].[C:8]1([SH:14])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)([O-])O.[Na+]>C1C=CC=CC=1>[C:8]1([S:14]/[CH:3]=[CH:4]/[C:5](=[O:7])[CH3:6])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of (E)-4-methoxy-3-buten-2-one (purity 90%, 5.66 ml, 49.9 mmol) and thiophenol (5.13 ml, 49.9 mmol) in benzene (60 ml) was added p-toluene 25 sulfonic acid-monohydrate (30 mg, 0.16 mmol), followed by heating while stirring on an oil bath at 55° C. for 30 minutes. After ice cooling, an aqueous saturated sodium hydrogen carbonate solution was added thereto, followed by extracting with cyclohexane 3 times. The organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution twice and with saturated brine, followed by drying with anhydrous magnesium sulfate. After concentrating under a reduced pressure, the residue was treated with the column chromatography (190 g, n-hexane:ethyl acetate=10:1). After evaporated under a reduced pressure, the titled compound was recrystallized from n-hexane-n-nonane to obtain as a colorless crystalline.

Workup

temperatureby heating
extractionby extracting with cyclohexane 3 times
washThe organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution twice
dry with materialby drying with anhydrous magnesium sulfate
concentrationAfter concentrating under a reduced pressure
additionthe residue was treated with the column chromatography (190 g, n-hexane:ethyl acetate=10:1)
customAfter evaporated under a reduced pressure
customthe titled compound was recrystallized from n-hexane-n-nonane
customto obtain as a colorless crystalline

Sources & evidence

ORD record: ord-280fc3a25aeb4ca6ab03b6a3c0115de6
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06049009

Reaction notes

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