m-Chloroperbenzoic acid → (3,4-Dihydro-2,5-dimethyl-2H-1-benzopyran-8-yl)diazenecarboxylic acid methyl ester

HRID 637632노트

반응식

HRID 637632 반응식
[CH:1]1C=C(Cl)C=C(C(OO)=O)C=1.[CH3:12][CH:13]1[CH2:18][CH2:17][C:16]2[C:19]([CH3:28])=[CH:20][CH:21]=[C:22]([NH:23][NH:24][C:25]([OH:27])=[O:26])[C:15]=2[O:14]1>C(Cl)Cl>[CH3:1][O:26][C:25]([N:24]=[N:23][C:22]1[C:15]2[O:14][CH:13]([CH3:12])[CH2:18][CH2:17][C:16]=2[C:19]([CH3:28])=[CH:20][CH:21]=1)=[O:27]

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 202555732-(3,4-dihydro-2,5-dimethyl-2H-1-benzopyran-8-yl)hydrazinecarboxylic acid

생성물 1

HCID 13560300(3,4-Dihydro-2,5-dimethyl-2H-1-benzopyran-8-yl)diazenecarboxylic acid methyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
35 °C

실험 절차

A solution of 13.8 g of MCPBA in 100 ml of methylene chloride was added drop-by-drop over 10 minutes to a stirred solution of 16.1 g of 1G in 150 ml of methylene chloride at room temperature. The resulting mixture was stirred and refluxed (35° C.) for 30 minutes, then washed with 10% aqueous sodium carbonate solution. The resulting methylene chloride solution was dried (MgSO4), and the solvent was evaporated. The residue was purified by column chromatography over silica gel, using a 1:4:20 v:v:v mixture of THF, ethyl acetate and hexane as eluent, to give 1, as a brick red solid, m.p.: 95°-97° C.

후처리

  1. washwashed with 10% aqueous sodium carbonate solution
  2. dry with materialThe resulting methylene chloride solution was dried (MgSO4)
  3. customthe solvent was evaporated
  4. customThe residue was purified by column chromatography over silica gel
  5. additionv:v mixture of THF, ethyl acetate and hexane as eluent
  6. customto give 1

출처 및 근거

ORD 기록
ord-72839abe6f764d64a8c1fde35a726db6
출처 데이터셋
uspto-grants-1985_12
특허 번호
US04558040

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