Potassium Carbonate → [4-(4-Ethanesulfonyl-phenoxy)-6-fluoro-naphthalen-2-yl]-acetic acid methyl ester

HRID 238599

반응식

HRID 238599 반응식
[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[CH:14]=[C:13]([OH:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:16])[CH:11]=2)[CH:6]=1.[CH2:18]([S:20]([C:23]1[CH:28]=[CH:27][C:26](F)=[CH:25][CH:24]=1)(=[O:22])=[O:21])[CH3:19].C(=O)([O-])[O-].[K+].[K+]>>[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[CH:14]=[C:13]([O:15][C:26]2[CH:25]=[CH:24][C:23]([S:20]([CH2:18][CH3:19])(=[O:22])=[O:21])=[CH:28][CH:27]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:16])[CH:11]=2)[CH:6]=1

참가 물질

4

반응물 3

HCID 11430Potassium CarbonateHCID 71814FluoresoneHCID 20335012HCID 20335012, 화합물

생성물 1

HCID 59326563[4-(4-Ethanesulfonyl-phenoxy)-6-fluoro-naphthalen-2-yl]-acetic acid methyl ester수율 80%

반응 조건

온도
100 °C

실험 절차

A sealed tube containing (6-fluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester (49 mg, 0.21 mmol), 1-ethanesulfonyl-4-fluoro-benzene (87 mg, 0.427 mmol), and potassium carbonate (73 mg, 0.53 mmol) was evacuated and filled with nitrogen. Anhydrous N,N-dimethylformamide (2 mL) was added. After being stirred at 100° C. overnight, the mixture was cooled to room temperature, then diluted with water (10 mL), and extracted with ethyl acetate (10 mL×2). The combined organic layers were washed with brine (10 mL×3), dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (elution with 30% ethyl acetate in petroleum ether) to give [4-(4-ethanesulfonyl-phenoxy)-6-fluoro-naphthalen-2-yl]-acetic acid methyl ester (67.6 mg, 80%) as a white solid.

후처리

  1. customwas evacuated
  2. additionfilled with nitrogen
  3. additionAnhydrous N,N-dimethylformamide (2 mL) was added
  4. temperaturethe mixture was cooled to room temperature
  5. additiondiluted with water (10 mL)
  6. extractionextracted with ethyl acetate (10 mL×2)
  7. washThe combined organic layers were washed with brine (10 mL×3)
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by column chromatography (elution with 30% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-9a9cc125734d470faa4abb24d4784594
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642629B2

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