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

HRID 2275241ノート

反応式

HRID 2275241 の反応式
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

参加物

6

反応物 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 66834047HCID 66834047、化合物HCID 178418339Butyllithium

生成物 1

HCID 668347002-(1-Benzo[b]thiophen-2-yl-1-methylethyl)-4-methoxy-benzoic acid収率 55%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-0b412adb78094b86bac513a59106581b
出典データセット
uspto-grants-2015_09
特許番号
US09126931B2

反応ノート

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