The synthesis of D-18954 is performed using dimethyl(2-fluoro-4-methoxy-phenyl)carbinol (I) as educt. The tertiary alcohol (I) can be obtained by Grignard reaction of 2-fluoro-4-methoxyacetophenone with methyl magnesium iodide. The dibenzyl derivative (II) is prepared by reductive coupling of (I) using TiCl3-LiAlH4, according to the method of McMurry and Silvestri. The cleavage of the methoxy groups is accomplished with BBr3 and gives D-18954.
The tertiary alcohol (I) can be obtained by Grignard reaction of methyl 4-methoxybenzoate with methylmagnesium iodide. The bibenzyl derivative (II) is prepared by reductive coupling of (I) using TiCl3 - LiAlH4, according to the method of McMurry and Silvestri. The cleavage of the methoxy groups is performed with BBr3 and gives tetramethylHES.