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

온도

60 °C

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.

1. customThis compound was prepared in a fashion similar to Example 1 with the following modifications
2. customThe solvent was removed
3. customthe mixture was partitioned between EtOAc and 1N HCl
4. washThe EtOAc was washed with H2O
5. dry with materialdried (MgSO4)
6. customthe solvent removed

ORD 기록

ord-b33b184bf2e848e49950ee333a227880

출처 데이터셋

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07459567B2