Dimethyl Sulfoxide → Methane, sulfinylbis-, ion(1-), sodium

HRID 854956

Reaktionsgleichung

[CH3:1]CCCCC.[H-].[Na+:8].[CH3:9][O:10][C:11]1[CH:12]=[C:13]([C:17]([CH3:21])([CH3:20])[CH:18]=O)[CH:14]=[CH:15][CH:16]=1.[CH3:22][S:23]([CH3:25])=[O:24]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:22][S:23]([CH2-:25])=[O:24].[Na+:8].[CH3:20][C:17]([C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([O:10][CH3:9])[CH:12]=1)([CH3:21])[CH:18]=[CH2:1]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

A solution of sodium dimsylate was prepared by dissolving hexane washed 60% NaH (4.89 g, 122 mmoles) in mineral oil in 120 mL of DMSO with heating to 60° C. To 40 mL of this solution added methyltriphenylphosphonium bromide (14.5 g, 40.7 mmoles) of as a solid, forming a thick paste. A solution of 2-(3-methoxyphenyl)-2-methylpropanal (5.00 g, 28.1 mmoles) in 6 mL of DMSO was added, and the mixture stirred overnight. The mixture was partitioned between Et2O and water, and the aqueous layer further extracted with Et2O. The combined organic extracts were washed with water and brine, dried over Na2SO4, filtered, and evaporated. Chromatography of the residue over silica gel using DCM as eluent gave 1-(1,1-dimethylprop-2-enyl)-3-methoxybenzene, 4.25 g, as an oil.

Aufarbeitung

customforming a thick paste
customThe mixture was partitioned between Et2O and water
extractionthe aqueous layer further extracted with Et2O
washThe combined organic extracts were washed with water and brine
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-e8c2f21d9c0f4562bb95578756d53a1e
Quelldatensatz: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07259266B2

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