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

HRID 2275241노트

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HRID 2275241 반응식
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

참가 물질

6

반응물 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 66834047HCID 66834047, 화합물HCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-0b412adb78094b86bac513a59106581b
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126931B2

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