Methylparaben → Methyl 4-[3-(4-chlorophenyl)-2-oxooxazolidin-5-yl]methoxybenzoate

HRID 374494노트

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HRID 374494 반응식
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:15][CH:16]1[O:20][C:19](=[O:21])[N:18]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[CH2:17]1>CN(C)C=O>[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([N:18]2[CH2:17][CH:16]([CH2:15][O:1][C:2]3[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=3)[O:20][C:19]2=[O:21])=[CH:27][CH:26]=1

참가 물질

5

반응물 3

HCID 7456MethylparabenHCID 24758Sodium hydrideHCID 189972075-(Chloromethyl)-3-(4-chlorophenyl)-1,3-oxazolidin-2-one

생성물 1

HCID 15281823Methyl 4-[3-(4-chlorophenyl)-2-oxooxazolidin-5-yl]methoxybenzoate수율 48%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
40 °C

실험 절차

A 1.52 g quantity of methyl 4-hydroxy-benzoate was added to a suspension of 0.42 g of 60% sodium hydride in anhydrous N,N-dimethylformamide (15 ml) with ice-cooling in a stream of nitrogen. To the mixture was added dropwise an anhydrous N,N-dimethylformamide (15 ml) solution of 2.46 g of 5-(chloromethyl)-3-(4-chlorophenyl)-2-oxooxazolidine obtained in Reference Example 7 at the same temperature, and the mixture was stirred at 40° C. for 48 hours. The reaction mixture was concentrated under reduced pressure, and the obtained residue was extracted with ethyl acetate. The extract was washed with water, dried with magnesium sulfate and filtered. The filtrate was then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and purified by hexane-ethyl acetate gradient elution to give 1.75 g of the title compound (compound 51) in a yield of 48%.

후처리

  1. temperaturecooling in a stream of nitrogen
  2. customobtained in Reference Example 7 at the same temperature
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. extractionthe obtained residue was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was then concentrated under reduced pressure
  9. custompurified by hexane-ethyl acetate gradient elution

출처 및 근거

ORD 기록
ord-a24dde527a194a25bb39044f651ab2b4
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05480899

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