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Acetic Acid → Methyl 3-[1-(4-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-(pyrid-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropionate

HRID 1975740
ノート
印刷プレビュー

反応式

HRID 1975740 の反応式
[C:1]([S:5][CH2:6][C:7](=O)[CH2:8][C:9]([CH3:15])([CH3:14])[C:10]([O:12][CH3:13])=[O:11])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.C([O-])(=O)C.[Na+].[Cl:26][C:27]1[CH:49]=[CH:48][C:30]([CH2:31][N:32]([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=3)=[CH:36][CH:35]=2)N)=[CH:29][CH:28]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.CCCCCC.O>[Cl:26][C:27]1[CH:49]=[CH:48][C:30]([CH2:31][N:32]2[C:34]3[C:39](=[CH:38][C:37]([O:40][CH2:41][C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=4)=[CH:36][CH:35]=3)[C:6]([S:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[C:7]2[CH2:8][C:9]([CH3:15])([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:29][CH:28]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 14980531Methyl 5-t-butylthio-2,2-dimethyl-4-oxopentanoateHCID 190983301-(4-Chlorobenzyl)-1-[4-(pyrid-2-ylmethoxy)phenyl] hydrazine

生成物 1

HCID 19098332Methyl 3-[1-(4-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-(pyrid-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropionate

試薬・触媒・溶媒 3

HCID 962Water溶媒
HCID 1140Toluene溶媒
HCID 21226206Ethyl acetate hexane溶媒

実験手順

To a solution of methyl 5-t-butylthio-2,2-dimethyl-4-oxopentanoate (33.2 g; 135 mmol), prepared as in Example 1, step 4, in 300 mL toluene and 150 mL acetic acid was added sodium acetate (12.7 g; 155 mmol) followed by 1-(4-chlorobenzyl)-1-[4-(pyrid-2-ylmethoxy)phenyl] hydrazine (48.4 g; 143 mmol), prepared as in step 4. The reaction mixture was stirred in the dark for 5 days, then was poured into water and extracted with ethyl acetate. Solid sodium bicarbonate was added to the extracts and then filtered. The filtrate was washed with water, dried over magnesium sulfate, and the solvent was evaporated. The product was isolated by flash chromatography (40% diethyl ether in hexane) and then recystallized from ethyl acetate/hexane to yield methyl 3-[1-(4-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-(pyrid-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropionate.

後処理

  1. extractionextracted with ethyl acetate
  2. additionSolid sodium bicarbonate was added to the extracts
  3. filtrationfiltered
  4. washThe filtrate was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe product was isolated by flash chromatography (40% diethyl ether in hexane)

出典と根拠

ORDレコード
ord-a48a416db2384b2880eeafea8ce50e51
出典データセット
uspto-grants-1994_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05288743

反応ノート

読み込み中…

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