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Cesium carbonate → 2-Methyl-4-(pyridin-2-yloxy)-benzoic acid ethyl ester

HRID 1480975
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HRID 1480975 반응식
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[CH3:12])[CH3:2].I[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.CC(C)(C(=O)CC(=O)C(C)(C)C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1.CCOC(C)=O.Cl[Cu]>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:7][C:6]=1[CH3:12])[CH3:2]
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참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 2211262-IodopyridineHCID 13356900Ethyl 4-hydroxy-2-methylbenzoate

생성물 1

HCID 898129622-Methyl-4-(pyridin-2-yloxy)-benzoic acid ethyl ester

시약·촉매·용매 3

HCID 62652Cuprous chloride
촉매
HCID 8857Ethyl Acetate용매
HCID 13387N-methyl-2-pyrrolidone용매

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온도
120 °C

실험 절차

A mixture of 4-hydroxy-2-methyl-benzoic acid ethyl ester (400 mg), 2-iodo-pyridine (0.29 mL), CuCl (110 mg), 2,2,6,6-tetramethyl-heptane-3,5-dione (TMHD, 0.087 mL), cesium carbonate (940 mg) in NMP (2 mL) was heated at 120° C. for 20 h. Then the reaction was cooled, diluted with EtOAc, solids were filtered off, filtrate was washed with water, diluted NaCl solution, dried over sodium sulfate, filtered off, concentrated, the residue was column purified to give the desired product (531 mg). LC MS ESI+: 258 (M+1)+.

후처리

  1. temperatureThen the reaction was cooled
  2. filtrationwere filtered off
  3. washfiltrate was washed with water, diluted NaCl solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered off
  6. concentrationconcentrated
  7. custompurified

출처 및 근거

ORD 기록
ord-c9b0bb9f2ca34bcfaab8c9fa8d3220bf
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09409892B2

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