Water → ethyl hydroxy-(1-methyl-2-phenyl-1H-indol-3-yl)-acetate

HRID 590978

反応式

HRID 590978 の反応式
[BH4-].[BH4-].[BH4-].[BH4-].[Na+].[Na+].[Na+].[Na+].[CH3:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:19](=[O:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:11]1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O>O1CCCC1.CO>[OH:25][CH:19]([C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:10]([CH3:9])[C:11]=1[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21]

参加物

6

反応物 3

HCID 962WaterHCID 70855253ethyl (1-methyl-2-phenyl-1H-indol-3-yl)-oxo-acetateHCID 131720822Sodium tetraborohydride

生成物 1

HCID 70855247ethyl hydroxy-(1-methyl-2-phenyl-1H-indol-3-yl)-acetate収率 69.3%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

At 0° C., sodium tetraborohydride (78 mg, 2 mmol) was added to a solution of ethyl (1-methyl-2-phenyl-1H-indol-3-yl)-oxo-acetate (8a) (630 mg, 2.05 mmol) in a mixture of tetrahydrofuran (10 mL) and methanol (15 mL). The mixture was stirred at room temperature for 2 hours and then hydrolyzed with water. Methanol and tetrahydrofuran were removed under reduced pressure and the residue was diluted with dichloromethane. The organic layer was washed with water, brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (dichloromethane) to afford the desired alcohol (8b) (440 mg, 1.42 mmol, 69%).

後処理

  1. customMethanol and tetrahydrofuran were removed under reduced pressure
  2. additionthe residue was diluted with dichloromethane
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel (dichloromethane)

出典と根拠

ORDレコード
ord-28973bfa09cd4955b5bf124020eadc92
出典データセット
uspto-grants-2016_01
特許番号
US09238026B2

関連ノート

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