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

HRID 2373705Notes

Reaction equation

[Si](OC1C=CC(B(O)O)=CC=1)(C(C)(C)C)(C)C.BrC1C(CC(OC)=O)=C(C2C=CC(O[Si](C(C)(C)C)(C)C)=CC=2)SC=1.ClC1C=CC=CC=1B(O)O.[Si]([O:60][C:61]1[CH:66]=[CH:65][C:64]([C:67]2[S:68][CH:69]=[C:70]([C:77]3[CH:82]=[CH:81][CH:80]=[CH:79][C:78]=3[Cl:83])[C:71]=2[CH2:72][C:73]([O:75][CH3:76])=[O:74])=[CH:63][CH:62]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:83][C:78]1[CH:79]=[CH:80][CH:81]=[CH:82][C:77]=1[C:70]1[C:71]([CH2:72][C:73]([O:75][CH3:76])=[O:74])=[C:67]([C:64]2[CH:65]=[CH:66][C:61]([OH:60])=[CH:62][CH:63]=2)[S:68][CH:69]=1

Participants

Conditions

Temperature: 60 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-b33b184bf2e848e49950ee333a227880
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459567B2

Reaction notes

Loading…