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Hydrochloric Acid → 3-(2-Benzofuran-1(3H)-ylidene)-5-methoxy-1,3-dihydro-2H-indol-2-one

HRID 1829013
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HRID 1829013 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6]2.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C1COCC1.[C:28]1([C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:31][O:30]1)=O.Cl>C1COCC1.O>[C:28]1(=[C:6]2[C:5]3[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=3)[NH:8][C:7]2=[O:12])[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:31][O:30]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6885PhthalideHCID 15142865-MethoxyoxindoleHCID 23714775LiHMDS tetrahydrofuran

생성물 1

HCID 696593173-(2-Benzofuran-1(3H)-ylidene)-5-methoxy-1,3-dihydro-2H-indol-2-one수율 46%

시약·촉매·용매 2

HCID 962Water
용매
HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirred solution of 5-methoxyoxindole (100 mg, 0.61 mmol) in anhydrous THF (5 ml) under nitrogen was added 1.0M LiHMDS/THF solution (1.3 ml, 1.3 mmol). The mixture was stirred at room temperature for 10 minutes, and phthalide (74 mg, 0.55 mmol) was added. The mixture was stirred at room temperature for 5 hours and was then poured into a mixture of THF (10 ml) and 2M HCl (10 ml). The mixture was heated at 45° C. for 30 minutes, cooled to room temperature, and poured into water (125 ml). The resulting solid was separated, washed with water and dried under vacuum to give 3-(3H-Isobenzofuran-1-ylidene)-5-methoxy-1,3-dihydro-indol-2-one (70 mg, 46%).

후처리

  1. stirringThe mixture was stirred at room temperature for 5 hours
  2. temperatureThe mixture was heated at 45° C. for 30 minutes
  3. temperaturecooled to room temperature
  4. customThe resulting solid was separated
  5. washwashed with water
  6. customdried under vacuum

출처 및 근거

ORD 기록
ord-e9ef2712fb87429c83c586f0d17a862f
출처 데이터셋
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07060844B2

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