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Water → Ethyl 2-ethyl-4-[4-(methylsulfonyl)phenoxy]-1-benzofuran-6-carboxylate

HRID 1643737
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HRID 1643737 반응식
[CH2:1]([C:3]1[O:4][C:5]2[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:9]=[C:8]([OH:17])[C:6]=2[CH:7]=1)[CH3:2].[CH3:18][S:19]([C:22]1[CH:27]=[CH:26][C:25](F)=[CH:24][CH:23]=1)(=[O:21])=[O:20].C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[CH2:1]([C:3]1[O:4][C:5]2[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:9]=[C:8]([O:17][C:25]3[CH:26]=[CH:27][C:22]([S:19]([CH3:18])(=[O:21])=[O:20])=[CH:23][CH:24]=3)[C:6]=2[CH:7]=1)[CH3:2]
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참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 679941-Fluoro-4-(methylsulphonyl)benzeneHCID 59560005Ethyl 2-ethyl-4-hydroxy-1-benzofuran-6-carboxylate

생성물 1

HCID 59560127Ethyl 2-ethyl-4-[4-(methylsulfonyl)phenoxy]-1-benzofuran-6-carboxylate수율 60.6%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
100 °C

실험 절차

A mixture of ethyl 2-ethyl-4-hydroxy-1-benzofuran-6-carboxylate (0.80 g, 3.4 mmol), 4-fluorophenyl methyl sulfone (0.60 g, 3.4 mmol) and Cs2CO3 (1.12 g, 3.4 mmol) in DMF (40 mL) was heated to 100° C. overnight. The reaction was monitored by TLC (petroleum ether/EtOAc 4:1). The mixture was poured into water (50 mL) and extracted with EtOAc (90 mL×3). The organic layer was washed with brine (50 mL×2), dried over Na2SO4 and concentrated. The product was purified via column chromatography on silica gel eluted with petroleum ether/EtOAc (20:1) to afford the desired compound (0.80 g, 60%) as a colorless oil.

후처리

  1. extractionextracted with EtOAc (90 mL×3)
  2. washThe organic layer was washed with brine (50 mL×2)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe product was purified via column chromatography on silica gel
  6. washeluted with petroleum ether/EtOAc (20:1)

출처 및 근거

ORD 기록
ord-30a9b09330954a2babf1bbc22dee617c
출처 데이터셋
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08119624B2

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