Dimethylformamide → 1-(Benzyloxy)-2-{[(2,6-dichlorophenyl)methoxy]methyl}butan-2-ol
Reaktionsgleichung
[Cl:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:3]=1[CH2:4][O:5][CH2:6][C:7]([CH3:11])([OH:10])[CH2:8][OH:9].[H-].[Na+].[CH2:19](Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH3:27]N(C)C=O>>[Cl:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:3]=1[CH2:4][O:5][CH2:6][C:7]([CH2:11][CH3:27])([OH:10])[CH2:8][O:9][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1Komponenten
5
Versuchsvorschrift
1-(2,6-Dichlorobenzyloxymethyl)-1-methylethane-1,2-diol (14g) in dimethyl formamide (80 ml) was treated with sodium hydride (1.3 g) at ambient temperature and stirred for 12 h. Benzyl chloride (8 g) was then added and the reaction mixture stirred for a further 4 h. The solvent was then evaporated and 1-(2,6-dichlorobenzyloxy)-3 -benzyloxy-2-ethylpropan-2-ol isolated as a colourless oil by chromatography on silica gel eluted with 9/1 methylene chloride/ether. The structure was confirmed by n.m.r. techniques.