Tetrabutylammonium Fluoride → Methyl [4-(2-chlorophenyl)-2-(4-hydroxyphenyl)thien-3-yl]acetate

Participants

Reaction Conditions

Reaction Steps

This compound was prepared in a fashion similar to Example 1 with the following modifications: 4(t-Butyldimethylsilyloxy)phenylboronic acid (2.53 g, 10.0 mmol) was used in Step 5 to synthesize methyl [4-bromo-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)thien-3-yl]acetate (2.71 g). This material was reacted as in Example 1 Step 6 with 2-chlorophenylboronic acid (1.93 g, 12.31 mmol) to synthesize methyl [2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-(2-chlorophenyl)thien-3-yl]acetate (2.12 g). Methyl [2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-(2-chlorophenyl)thien-3-yl]acetate (2.00 g, 4.22 mmol) was dissolved in THF and a solution of tetrabutylammonium fluoride in THF (4.65 mL, 1 M, 4.65 mmol) was added dropwise. The solution was heated to 60° C. and stirred for 3 h. The solvent was removed and the mixture was partitioned between EtOAc and 1N HCl. The EtOAc was washed with H2O, dried (MgSO4), and the solvent removed to yield methyl [4-(2-chlorophenyl)-2-(4-hydroxyphenyl)thien-3-yl]acetate (1.34 g) which was used without further purification.

Provenance & Evidence