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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
ノート
印刷プレビュー

反応式

HRID 434018 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 18756449Dichloromethane morpholine water溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-b90100b1a1374342bc64ac8a774486ba
出典データセット
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06670388B1

反応ノート

読み込み中…

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