Tetrahydrofuran → 2-{6,6-dimethyl-1-[2-(trimethylsilyl)ethoxymethyl]-4,5,6,7-tetrahydro-1H-indazol-3-yl}-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indole-6-carboxylic acid

HRID 2068879ノート

反応式

HRID 2068879 の反応式
[CH3:1][C:2]1([CH3:40])[CH2:10][C:9]2[N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[N:7]=[C:6]([C:19]3[N:20]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:21]4[C:26]([CH:27]=3)=[CH:25][CH:24]=[C:23]([C:28]([O:30]C)=[O:29])[CH:22]=4)[C:5]=2[CH2:4][CH2:3]1.O1CCCC1.[OH-].[Na+]>CO>[CH3:1][C:2]1([CH3:40])[CH2:10][C:9]2[N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:16])([CH3:17])[CH3:18])[N:7]=[C:6]([C:19]3[N:20]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:37])([CH3:39])[CH3:38])[C:21]4[C:26]([CH:27]=3)=[CH:25][CH:24]=[C:23]([C:28]([OH:30])=[O:29])[CH:22]=4)[C:5]=2[CH2:4][CH2:3]1

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 58550118methyl 2-{6,6-dimethyl-1-[2-(trimethylsilyl)ethoxymethyl]-4,5,6,7-tetrahydro-1H-indazol-3-yl}-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indole-6-carboxylate

生成物 1

HCID 585502432-{6,6-dimethyl-1-[2-(trimethylsilyl)ethoxymethyl]-4,5,6,7-tetrahydro-1H-indazol-3-yl}-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indole-6-carboxylic acid収率 97%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

To a solution of methyl 2-{6,6-dimethyl-1-[2-(trimethylsilyl)ethoxymethyl]-4,5,6,7-tetrahydro-1H-indazol-3-yl}-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indole-6-carboxylate (33 g, 57 mmol) in a mixed solvent of tetrahydrofuran (165 ml) and methanol (165 ml) was added 4 N aqueous sodium hydroxide solution (71 ml, 284 mmol), and the mixture was heated at 60° C. for 2 hr. After cooling, the reaction mixture was concentrated, 10% aqueous citric acid solution was added to the residue to adjust the pH to 5, and the mixture was extracted with ethyl acetate. Then, the organic layer was washed with saturated brine, and dried over sodium sulfate. Sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure to give the title compound (31 g, yield 97%).

後処理

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated
  3. addition10% aqueous citric acid solution was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThen, the organic layer was washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. customSodium sulfate was removed by filtration
  8. concentrationthe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-5dba88e0fa7649a1a7f405f491375545
出典データセット
uspto-grants-2012_10
特許番号
US08299070B2

反応ノート

読み込み中…