4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid 4-(6-methoxy-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin-1-yl)phenyl ester

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Reaction Steps

A solution of 2,2,2-trifluoro-1-[1-(4-hydroxyphenyl)-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl]ethanone (3.387 g, 9.64 mmol), p-toluenesulfonyl chloride (2.206 g, 11.6 mmol) and Et3N (1.6 ml, 11.6 mmol) in acetone (50 ml) was refluxed under N2 for 5 hr, then concentrated in vacuo. The remaining residue was suspended in H2O (100 ml) and extracted with CHCl3 (4×75 ml). The combined extracts were dried over MgSO4 and concentrated in vacuo to give 5.622 g of orange oil. Purification by flash chromatography, eluting with hexane:EtOAc (8:2) gave 4.383 g (90% yield) of white solid.

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