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

HRID 234479

反応式

HRID 234479 の反応式
[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]

参加物

8

反応物 4

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

生成物 2

HCID 219059555-Chloro-3-hydroxy-3-(2-methoxyphenyl)indolin-2-oneHCID 178489560HCID 178489560、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-af335294599a403084827c600955337f
出典データセット
uspto-grants-1997_01
特許番号
US05594023

関連ノート

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