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Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → [2-(4-Methoxyphenyl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]acetic acid

HRID 280536
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HRID 280536 반응식
O[CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.C([O:22][C:23]([CH:25]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:24])C>C1(C)C=CC=CC=1>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:2]([CH2:25][C:23]([OH:24])=[O:22])[N:3]1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1
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참가 물질

4

반응물 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 3688143HCID 3688143, 화합물

생성물 1

HCID 14815080[2-(4-Methoxyphenyl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]acetic acid수율 87.9%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A solution of 3-hydroxy-2-(4-methoxyphenyl)isoindolin-1-one (12.0 g) and ethoxycarbonylmethylenetriphenylphosphorane (16.0 g) in toluene (200 ml) was refluxed for 3 hours. After cooling, the toluene was distilled off and the residue was dissolved in 100 ml of methanol. A solution of 10 g of potassium carbonate in 70 ml of water was added to the above methanol solution and the mixture was refluxed gently for an hour. After cooling, 200 ml of water and 300 ml of ether were added and the mixture was shaken well. The aqueous layer was separated and acidified with 5N hydrochloric acid to give 12 g of 3oxo-2-(4-methoxyphenyl)isoindoline-1-acetic acid, which was described in (iv) of Example 2.

후처리

  1. temperatureAfter cooling
  2. distillationthe toluene was distilled off
  3. dissolutionthe residue was dissolved in 100 ml of methanol
  4. additionA solution of 10 g of potassium carbonate in 70 ml of water was added to the above methanol solution
  5. temperaturethe mixture was refluxed gently for an hour
  6. temperatureAfter cooling
  7. addition200 ml of water and 300 ml of ether were added
  8. customThe aqueous layer was separated

출처 및 근거

ORD 기록
ord-99d02381671a4c3f9ee58b2a562bfb09
출처 데이터셋
uspto-grants-1986_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04590189

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