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Methyl iodide → Methyl 2-{4-[1-(4-iodophenyl)-1,2-dimethylpropyl]phenoxy}-2-pyridin-2-ylpropanoate

HRID 1025806
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HRID 1025806 반응식
[CH:1]([N-]C(C)C)(C)C.[Li+].[I:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:21]2[CH:38]=[CH:37][C:24]([O:25][CH:26]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=3)[C:27]([O:29][CH3:30])=[O:28])=[CH:23][CH:22]=2)([CH3:20])[CH:17]([CH3:19])[CH3:18])=[CH:12][CH:11]=1.CN1CCCN(C)C1=O.IC>C1CCCCC1.C1COCC1>[I:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]([C:21]2[CH:22]=[CH:23][C:24]([O:25][C:26]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=3)([CH3:1])[C:27]([O:29][CH3:30])=[O:28])=[CH:37][CH:38]=2)([CH3:20])[CH:17]([CH3:18])[CH3:19])=[CH:14][CH:15]=1
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참가 물질

7

반응물 4

HCID 6328Methyl iodideHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 2724682Lithium diisopropylamideHCID 58381245Methyl {4-[1-(4-iodophenyl)-1,2-dimethylpropyl]phenoxy}(pyridin-2-yl)acetate

생성물 1

HCID 58381237Methyl 2-{4-[1-(4-iodophenyl)-1,2-dimethylpropyl]phenoxy}-2-pyridin-2-ylpropanoate

시약·촉매·용매 2

HCID 8028
Tetrahydrofuran
용매
HCID 8078Cyclohexane용매

실험 절차

Lithium diisopropylamide mono (THF) (1.2 equiv. of a 5M solution in cyclohexane) is added to a stirred solution of 5c (1 equiv.) in THF at −78° C. After 15 mins, 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (1 equiv.) is added followed by iodomethane (1.5 equiv). After 1 h, the reaction mixture is warmed to room temperature and aged until the reaction is deemed complete. The reaction mixture is quenched with saturated aqueous ammonium chloride, poured into saturated aqueous sodium bicarbonate and extracted three times with EtOAc. The combined organic extracts are washed with water, brine, dried (Na2SO4) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel affords the title compound 5d.

후처리

  1. waitAfter 1 h
  2. customThe reaction mixture is quenched with saturated aqueous ammonium chloride
  3. additionpoured into saturated aqueous sodium bicarbonate
  4. extractionextracted three times with EtOAc
  5. washThe combined organic extracts are washed with water, brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude residue by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-ca194893fd8f4caaae58fc8a94e40389
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08729104B2

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