Tetrahydrofuran → 5-Chloro-3-hydroxy-3-(2-methoxyphenyl)indolin-2-one

HRID 234479

반응식

HRID 234479 반응식
[Mg:1].[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10].[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[C:15]2=[O:22].C1[CH2:27][O:26]CC1>CCOCC.O>[CH3:27][O:26][C:12]1[CH:13]=[CH:14][CH:18]=[CH:19][C:20]=1[Mg:1][Br:2].[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[C:15]2([OH:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10]

참가 물질

8

반응물 4

HCID 8028TetrahydrofuranHCID 113582-BromoanisoleHCID 872035-chloro-1H-indole-2,3-dioneHCID 5462224Magnesium

생성물 2

HCID 219059555-Chloro-3-hydroxy-3-(2-methoxyphenyl)indolin-2-oneHCID 178489560HCID 178489560, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매

실험 절차

A solution of 2-methoxyphenylmagnesium bromide is prepared from 1.35 g of magnesium and 10.5 g of 1-bromo-2-methoxybenzene in 100 ml of ether. This solution is added in 10 minutes at RT, under an argon atmosphere, to a mixture of 4.1 g of 5-chloroisatin and 70 ml of THF. After stirring for 1 hour at RT, water is added and the product is filtered off, redissolved in THF, dried over magnesium sulfate and evaporated under vacuum in the presence of iso ether. The residue is chromatographed on silica using a DCM/AcOEt mixture (60/40; v/v) as the eluent to give the expected product after crystallization from a THF/iso ether mixture.

후처리

  1. filtrationthe product is filtered off
  2. dissolutionredissolved in THF
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under vacuum in the presence of iso ether
  5. customThe residue is chromatographed on silica using a DCM/AcOEt mixture (60/40; v/v) as the eluent

출처 및 근거

ORD 기록
ord-af335294599a403084827c600955337f
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05594023

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