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Methyl iodide → 4-(Tert-butoxy)-3-methyl-4-oxobutanoic acid

HRID 2384077
ノート
印刷プレビュー

反応式

HRID 2384077 の反応式
[Li+].[CH3:2]C([N-]C(C)C)C.[C:9]([O:13][C:14](=[O:20])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])([CH3:12])([CH3:11])[CH3:10].CI>C1COCC1>[C:9]([O:13][C:14](=[O:20])[CH:15]([CH3:2])[CH2:16][C:17]([OH:19])=[O:18])([CH3:12])([CH3:10])[CH3:11]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 41391074-(Tert-butoxy)-4-oxobutanoic acid

生成物 1

HCID 127614644-(Tert-butoxy)-3-methyl-4-oxobutanoic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-20 °C

実験手順

To a stirred solution of LDA (6.3 mmol, 2M in hexane) in THF (5 mL) at −78° C. is added a solution of succinic acid mono-tert-butyl ester (523 mg, 3 mmol) in THF (2 mL) dropwise. After the addition, the mixture is warmed to −20° C. slowly and stirred at −20° C. for 30 minutes. The solution is re-cooled to −78° C. and MeI (511 mg, 3.6 mmol) is added dropwise. The mixture is warmed to room temperature and stirred for 18 hours. The mixture is quenched with water and extracted with ethyl acetate. The organic layer is washed with water, brine, dried over MgSO4 and filtered. The solvent is removed under reduced pressure to give 2-methyl-succinic acid 1-tert-butyl ester.

後処理

  1. additionAfter the addition
  2. temperatureThe solution is re-cooled to −78° C.
  3. temperatureThe mixture is warmed to room temperature
  4. stirringstirred for 18 hours
  5. customThe mixture is quenched with water
  6. extractionextracted with ethyl acetate
  7. washThe organic layer is washed with water, brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customThe solvent is removed under reduced pressure

出典と根拠

ORDレコード
ord-e790142049e341c49e715f78b7845cef
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08263629B2

反応ノート

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