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Phenol → Methyl 2-(4-methyl-6-phenoxy-2-phenylpyrimidin-5-yl)pentanoate

HRID 1399644
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인쇄 미리보기

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HRID 1399644 반응식
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:15]1[C:20]([CH:21]([CH2:26][CH2:27][CH3:28])[C:22]([O:24][CH3:25])=[O:23])=[C:19]([CH3:29])[N:18]=[C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:16]=1>O1CCCC1.C(=O)([O-])O.[Na+]>[CH3:29][C:19]1[C:20]([CH:21]([CH2:26][CH2:27][CH3:28])[C:22]([O:24][CH3:25])=[O:23])=[C:15]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:16]=[C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:18]=1
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참가 물질

6

반응물 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 86665652Methyl 2-(4-chloro-6-methyl-2-phenylpyrimidin-5-yl)pentanoate

생성물 1

HCID 66955927Methyl 2-(4-methyl-6-phenoxy-2-phenylpyrimidin-5-yl)pentanoate수율 68.5%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매
HCID 516892
Sodium Bicarbonate
용매

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온도
100 °C

실험 절차

Phenol (0.141 g; 1.5 mmol) and cesium carbonate (0.489 g; 1.5 mmol) were added to a solution of methyl 2-(4-chloro-6-methyl-2-phenylpyrimidin-5-yl)pentanoate (0.159 g; 0.5 mmol) in tetrahydrofuran (1.5 mL) and heated in a seal tube to 100° C. for 18 h. The mixture was diluted with a saturated solution of sodium hydrogen carbonate and was extracted with ethyl acetate. The combined organics were washed with brine, dried over magnesium sulphate, filtered and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-40%) in heptane furnished 0.129 g (58%) of the title compound.

후처리

  1. extractionwas extracted with ethyl acetate
  2. washThe combined organics were washed with brine
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-40%) in heptane

출처 및 근거

ORD 기록
ord-4b930a33b41844bf9f4c291cf586b28c
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08906906B2

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