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5-Allyloxy-1-[(2-thiophen-3-yl)ethyl]-1h-indole-2-carboxylic acid ethyl ester → 5-Hydroxy-1-[(2-thiophen-3-yl)ethyl]-1h-indole-2-carboxylic acid ethyl ester

HRID 434018
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HRID 434018 반응식
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:19][CH2:20][C:21]2[CH:25]=[CH:24][S:23][CH:22]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15]CC=C)=[CH:10][CH:9]=2)=[O:5])[CH3:2]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClCCl.N1CCOCC1.O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:19][CH2:20][C:21]2[CH:25]=[CH:24][S:23][CH:22]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([OH:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 1

HCID 120944655-Allyloxy-1-[(2-thiophen-3-yl)ethyl]-1h-indole-2-carboxylic acid ethyl ester

생성물 1

HCID 120944625-Hydroxy-1-[(2-thiophen-3-yl)ethyl]-1h-indole-2-carboxylic acid ethyl ester수율 108.5%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 18756449Dichloromethane morpholine water용매

실험 절차

To 5-allyloxy-1-[(2-thiophen-3-yl)ethyl]-1H-indole-2-carboxylic acid ethyl ester (1.36 g, 3.8 mmol) was added a mixture of dichloromethane:morpholine:water (100:10:2, 50 mL) followed by the addition of tetrakis(triphenylphosphine) palladium (0) (300 mg). After stilling at room temperature for 18 h, the reaction was partitioned between dichloromethane and water. The organic layer was washed with HCl (3N), NaHCO3, brine and dried over Na2SO4. Purification by flash column chromatography (silica gel, 10-30% EtOAc/hexanes) yielded the desired product as a off-white solid (1.3 g, 86%).

후처리

  1. customthe reaction was partitioned between dichloromethane and water
  2. washThe organic layer was washed with HCl (3N), NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. customPurification by flash column chromatography (silica gel, 10-30% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-b90100b1a1374342bc64ac8a774486ba
출처 데이터셋
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06670388B1

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