Potassium Carbonate → Methyl [(5-nitro-1,2-benzisoxazol-3-yl)oxy]acetate

HRID 277365ノート

反応式

HRID 277365 の反応式
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][N:10]=[C:9]([OH:12])[C:8]=2[CH:13]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]([O:24][CH3:25])=[O:23]>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][N:10]=[C:9]([O:12][CH2:21][C:22]([O:24][CH3:25])=[O:23])[C:8]=2[CH:13]=1)([O-:3])=[O:2]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 178526505HCID 178526505、化合物

生成物 1

HCID 53638345Methyl [(5-nitro-1,2-benzisoxazol-3-yl)oxy]acetate収率 50.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 5-nitro-1,2-benzisoxazol-3-ol (3.90 g, 0.0220 mol) and potassium carbonate (4.17 g, 0.0300 mol) in N,N-dimethylformamide is stirred for 30 minutes, treated with methyl bromoacetate (3.96 g, 0.0260 mol), stirred overnight at room temperature, and poured into an acidic ice-water mixture. The resultant aqueous mixture is extracted with ethyl acetate. The organic extracts are combined, washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a yellow oil. Column chromatography of the oil using silica gel and a (1:1) to (4:1) methylene chloride/hexanes gradient gives the title product as a white solid (2.80 g, mp 72-73.5° C.) which is identified by NMR spectral analyses.

後処理

  1. stirringstirred overnight at room temperature
  2. extractionThe resultant aqueous mixture is extracted with ethyl acetate
  3. washwashed sequentially with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a yellow oil

出典と根拠

ORDレコード
ord-5c1a532cbbc046b8b93dd3c61130726f
出典データセット
uspto-grants-2002_03
特許番号
US06355796B1

反応ノート

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