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Ethyl Acetate → 1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-hydroxyethyl-3-hydroxy-3-(2-naphthyl)oxindole

HRID 1369096
ノート
印刷プレビュー

反応式

HRID 1369096 の反応式
[CH2:1]([N:3]([CH2:36][CH3:37])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([C:20]([F:23])([F:22])[F:21])[CH:11]=[C:12](C(OCC)=O)[CH:13]=2)[C:8]([OH:34])([C:24]2[CH:33]=[CH:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=2)[C:7]1=[O:35])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.C([O-])(O)=O.[Na+].[C:53](OCC)(=[O:55])[CH3:54]>C1(C)C=CC=CC=1>[CH2:1]([N:3]([CH2:36][CH3:37])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([C:20]([F:21])([F:23])[F:22])[CH:11]=[C:12]([CH2:54][CH2:53][OH:55])[CH:13]=2)[C:8]([OH:34])([C:24]2[CH:33]=[CH:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=2)[C:7]1=[O:35])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 185186261-(2-Diethylaminoethyl)-4-trifluoromethyl-6-ethoxycarbonyl-3-hydroxy-3-(2-naphthyl)oxindoleHCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 185185581-(2-Diethylaminoethyl)-4-trifluoromethyl-6-hydroxyethyl-3-hydroxy-3-(2-naphthyl)oxindole収率 9%

試薬・触媒・溶媒

1
HCID 1140Toluene溶媒2 回

実験手順

To a solution of 1-(2-diethylaminoethyl)-4-trifluoromethyl-6-ethoxycarbonyl-3-hydroxy-3-(2-naphthyl)oxindole (605 mg, 0. 118 mmol) in toluene (1 mL) was added dropwise 1.01 N diisobutylaluminium hydride in toluene (0.36 mL, 0.364 mmol). The mixture was allowed to warm to room temperature over 4 h. Sat. aqueous NaHCO3 and ethyl acetate were added. Insoluble materials were removed by filtration and the organic layer was separated, dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography with 30:1 to 15:1 chloroform/methanol to give the title compound (5 mg, 9%).

後処理

  1. customInsoluble materials were removed by filtration
  2. customthe organic layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography with 30:1 to 15:1 chloroform/methanol

出典と根拠

ORDレコード
ord-6891bc95f20b46618c71b5fbe4a28de5
出典データセット
uspto-grants-2003_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06576656B1

反応ノート

読み込み中…

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