Sodium hydride → 5-Bromo-3,3-dimethyl-2-oxo-2,3-dihydroindol-1-ylmethyl 2,2-dimethylpropionate

HRID 40483

反応式

HRID 40483 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([CH3:13])[CH3:12].[H-].[Na+].[C:16]([O:22][CH2:23]Cl)(=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18]>CN(C)C=O>[CH3:18][C:17]([CH3:20])([CH3:19])[C:16]([O:22][CH2:23][N:7]1[C:8]2[C:4](=[CH:3][C:2]([Br:1])=[CH:10][CH:9]=2)[C:5]([CH3:13])([CH3:12])[C:6]1=[O:11])=[O:21]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 87885Chloromethyl pivalateHCID 120527965-bromo-3,3-dimethyl-2,3-dihydro-1H-indol-2-one

生成物 1

HCID 580317175-Bromo-3,3-dimethyl-2-oxo-2,3-dihydroindol-1-ylmethyl 2,2-dimethylpropionate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

1.0 g of 5-bromo-3,3-dimethyl-1,3-dihydroindol-2-one was dissolved in 100 ml of dimethylformamide, and 217 mg of sodium hydride (60% dispersion in mineral oil) were added. The mixture was then stirred at room temperature for 30 minutes. Then the reaction mixture was cooled to 0° C. in an ice bath, and 941 mg of chloromethyl pivalate were added. The ice bath was removed and the reaction mixture was stirred at room temperature for 30 minutes. Then the reaction mixture was diluted by adding 250 ml of ethyl acetate, and 50 ml of water were added. The organic phase was removed and washed once with 100 ml of saturated sodium chloride solution, dried over MgSO4 and then concentrated under reduced pressure. This gave 1.5 g of 5-bromo-3,3-dimethyl-2-oxo-2,3-dihydroindol-1-ylmethyl 2,2-dimethylpropionate.

後処理

  1. temperatureThen the reaction mixture was cooled to 0° C. in an ice bath
  2. customThe ice bath was removed
  3. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  4. additionThen the reaction mixture was diluted
  5. additionby adding 250 ml of ethyl acetate, and 50 ml of water
  6. additionwere added
  7. customThe organic phase was removed
  8. washwashed once with 100 ml of saturated sodium chloride solution
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-30420985f6444382afa7ed5065b6f1f2
出典データセット
uspto-grants-2013_09
特許番号
US08530413B2

関連ノート

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