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Water → 3-[(2E)-3-(4-tert-butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-en-1-yl]-1,3-oxazolidin-2-one

HRID 70698
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HRID 70698 반응식
[H-].[Na+].[O:3]1[CH2:7][CH2:6][NH:5][C:4]1=[O:8].Br[CH2:10]/[CH:11]=[C:12](/[C:23]1[N:28]=[C:27]([O:29][CH3:30])[C:26]([Cl:31])=[CH:25][CH:24]=1)\[C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=1.O>O1CCCC1>[C:19]([C:16]1[CH:15]=[CH:14][C:13](/[C:12](/[C:23]2[CH:24]=[CH:25][C:26]([Cl:31])=[C:27]([O:29][CH3:30])[N:28]=2)=[CH:11]\[CH2:10][N:5]2[CH2:6][CH2:7][O:3][C:4]2=[O:8])=[CH:18][CH:17]=1)([CH3:20])([CH3:21])[CH3:22]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 739492-OxazolidinoneHCID 584528146-[(1E)-3-Bromo-1-(4-tert-butylphenyl)prop-1-en-1-yl]-3-chloro-2-methoxypyridine

생성물 1

HCID 673984323-[(2E)-3-(4-tert-butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-en-1-yl]-1,3-oxazolidin-2-one수율 98%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

실험 절차

A suspension of sodium hydride (purity: 60%, 60 mg) in tetrahydrofuran (1.0 mL) was added to a solution of 2-oxazolidinone (153 mg) in tetrahydrofuran (1.0 mL) under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. 6-[(1E)-3-Bromo-1-(4-tert-butylphenyl)prop-1-en-1-yl]-3-chloro-2-methoxypyridine obtained in Reference Example 4-5 (303 mg) was added thereto, and the mixture was stirred at room temperature for 20 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→3:2) to give 3-[(2E)-3-(4-tert-butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-en-1-yl]-1,3-oxazolidin-2-one as a light brown powder (298 mg, 98%).

후처리

  1. temperaturecooling
  2. additionwas added
  3. stirringthe mixture was stirred at room temperature for 20 hours
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationAfter filtration
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→3:2)

출처 및 근거

ORD 기록
ord-ef25cd31208345898a90839280f8c46e
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08822503B2

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