Carbon Dioxide → 2-(1-Benzo[b]thiophen-2-yl-1-methylethyl)-4-methoxy-benzoic acid

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Reaktionsgleichung

Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]([C:13]1[S:17][C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=2[CH:14]=1)([CH3:12])[CH3:11].C([Li])CCC.[C:27](=[O:29])=[O:28].Cl>O1CCCC1>[S:17]1[C:13]([C:10]([C:3]2[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=2[C:27]([OH:29])=[O:28])([CH3:12])[CH3:11])=[CH:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]1=2

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

2-[1-(2-Bromo-5-methoxy-phenyl)-1-methylethyl]-benzo[b]thiophene (Compound Z3, 40 mg, 0.11 mmol) was dissolved in tetrahydrofuran (0.5 mL), cooled to −78° C., added with n-butyl lithium (1.57 M, hexane solution, 0.07 mL), and the mixture was stirred for 10 min. The reaction mixture was added with dry ice and then maintained for 1 hr. After that, the mixture was added with 0.5 N hydrochloric acid, extracted with ethyl acetate and washed with water. The organic layer was dried over magnesium sulfate. The residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (22 mg, 55%).

Aufarbeitung

temperaturemaintained for 1 hr
extractionextracted with ethyl acetate
washwashed with water
dry with materialThe organic layer was dried over magnesium sulfate
customThe residues obtained
concentrationafter concentration under reduced pressure
customwere purified by silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag: ord-0b412adb78094b86bac513a59106581b
Quelldatensatz: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09126931B2

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