1,2-Dimethoxyethane → 4-{2-[4-(Methanesulfonyl)phenyl]ethenyl}-N,N-dimethylaniline

Reaktionsgleichung

[H-].[Na+].[CH3:3][N:4]([C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1C=O)[CH3:5].[CH3:14][S:15]([C:18]1[CH:32]=[CH:31][C:21]([CH2:22]P(=O)(OCC)OCC)=[CH:20][CH:19]=1)(=[O:17])=[O:16].[CH3:33]OCCOC>>[CH3:5][N:4]([CH3:3])[C:6]1[CH:7]=[CH:10][C:11]([CH:33]=[CH:22][C:21]2[CH:20]=[CH:19][C:18]([S:15]([CH3:14])(=[O:16])=[O:17])=[CH:32][CH:31]=2)=[CH:12][CH:13]=1

Komponenten

Edukt 4

HCID 80711,2-Dimethoxyethane

HCID 24758Sodium hydride

HCID 34289Benzaldehyde, (dimethylamino)-

HCID 14419480(4-Methanesulfonylbenzyl)phosphonic acid diethyl ester

Produkt 1

HCID 537801194-{2-[4-(Methanesulfonyl)phenyl]ethenyl}-N,N-dimethylanilineAusbeute 66 %

Versuchsvorschrift

To a solution of 2.8 g (0.07 mol) of 60% sodium hydride dispersion, 7.46 g (0.05 mole) N,N-dimethylaminobenzaldehyde, and 100 mL of dry, freshly distilled 1,2-dimethoxyethane (DME) under nitrogen, at room temperature, was added 15.3 g (0.05 mole) diethyl 4-methylsulfonylbenzylphosphonate with vigorous stirring. The mixture immediately turned bright yellow. The mixture was heated at reflux for 2 hours. After cooling the very bright yellow solution was poured over 300 g of crushed ice under nitrogen blanket. The bright yellow solid was collected by filtration, washed with water, and air dried. Recrystallization from a 1:1 mixture of absolute ethanol and dry pyridine yielded 9.97 g (66%) of bright yellow crystals mp 242°-243° C.