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

HRID 1369096
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HRID 1369096 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매

1
HCID 1140Toluene용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-6891bc95f20b46618c71b5fbe4a28de5
출처 데이터셋
uspto-grants-2003_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06576656B1

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