Tetrabutylammonium Fluoride → 1-(2,4-Dichloro-3-hydroxymethylphenyl)2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole

HRID 365576ノート

反応式

HRID 365576 の反応式
[Si]([O:18][CH2:19][C:20]1[C:21]([Cl:48])=[C:22]([N:27]2[CH:31]=[CH:30][CH:29]=[C:28]2[CH2:32][NH:33][C:34](=[O:47])[CH:35]=[CH:36][C:37]2[CH:42]=[CH:41][C:40]([C:43](=[O:46])[NH:44][CH3:45])=[CH:39][CH:38]=2)[CH:23]=[CH:24][C:25]=1[Cl:26])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:48][C:21]1[C:20]([CH2:19][OH:18])=[C:25]([Cl:26])[CH:24]=[CH:23][C:22]=1[N:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[CH2:32][NH:33][C:34](=[O:47])[CH:35]=[CH:36][C:37]1[CH:38]=[CH:39][C:40]([C:43](=[O:46])[NH:44][CH3:45])=[CH:41][CH:42]=1

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 542764421-[3-(Tert-butyldiphenylsilyloxymethyl)-2,4-dichlorophenyl]-2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole

生成物 1

HCID 539366561-(2,4-Dichloro-3-hydroxymethylphenyl)2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole収率 48.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 1-[3-(tert-butyldiphenylsilyloxymethyl)-2,4-dichlorophenyl]-2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole (620 mg) in tetrahydrofuran (6 ml) was added 1N solution of tetrabutylammonium fluoride in tetrahydrofuran (2.5 ml). The mixture was stirred at ambient temperature for 6 hours and partitioned between ethyl acetate and water. The organic layer was isolated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with 1N hydrochloric acid and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with methanol to give 1-(2,4-dichloro-3-hydroxymethylphenyl)-2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole (197 mg) as a brownish powder.

後処理

  1. custompartitioned between ethyl acetate and water
  2. customThe organic layer was isolated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with 1N hydrochloric acid and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was triturated with methanol

出典と根拠

ORDレコード
ord-bddccdec49544842b767e860de4630b0
出典データセット
uspto-grants-2000_10
特許番号
US06127389

反応ノート

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