3-Furaldehyde → 2-(3-Furyl)-1-(methylsulfinyl)-1-(methylthio)ethylene

HRID 611051Notes

Reaction equation

[CH3:1][S:2]([CH2:4][S:5][CH3:6])=[O:3].[OH-].[Na+].[O:9]1[CH:13]=[CH:12][C:11]([CH:14]=O)=[CH:10]1>O>[O:9]1[CH:13]=[CH:12][C:11]([CH:14]=[C:4]([S:2]([CH3:1])=[O:3])[S:5][CH3:6])=[CH:10]1

Participants

Conditions

Temperature: 80 °C

Procedure

To 20 ml of methyl methylsulfinylmethyl sulfide, 1.34 g (33.5 mmol) of powdered sodium hydroxide was added, followed by stirring at 80° C. for 30 minutes. This mixture was added to 9.627 g (100.2 mmol) of 3-furaldehyde, followed by stirring at 80° C. for 3 hours. After this was cooled to room temperature, water was added, followed by 3 extractions with dichloromethane. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/2) to yield 2-(3-furyl)-1-(methylsulfinyl)-1-(methylthio)ethylene.

Workup

stirringby stirring at 80° C. for 3 hours
temperatureAfter this was cooled to room temperature
extractionfollowed by 3 extractions with dichloromethane
dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/2)

Sources & evidence

ORD record: ord-d44b04581d904829be8032796c8f84b8
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05998433

Reaction notes

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