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

HRID 374494ノート

反応式

HRID 374494 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
40 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-a24dde527a194a25bb39044f651ab2b4
出典データセット
uspto-grants-1996_01
特許番号
US05480899

反応ノート

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