Methyl iodide → 5-Methoxy-2-methylindan-1-one

HRID 643928

反応式

HRID 643928 の反応式
[CH:1](NC(C)C)(C)C.[Li]CCCC.[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[C:20](=[O:24])[CH2:19][CH2:18]2.CI.[NH4+].[Cl-]>C1COCC1>[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[C:20](=[O:24])[CH:19]([CH3:1])[CH2:18]2

参加物

7

反応物 5

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 787875-Methoxyindan-1-oneHCID 178418339Butyllithium

生成物 1

HCID 122904905-Methoxy-2-methylindan-1-one収率 43.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of diisopropylamine (5.2 mL, 36.9 mmol), in THF (20 mL) is added n-BuLi (14.8 mL, 36.9 mmol, 2.5 M in hexane) at −78° C. After 30 min, 5-methoxyindan-1-one (5.0 g, 30.8 mmol) in THF (35 mL) is added. After it is stirred at −78° C. for 1 h, the mixture is warmed to 10° C. for 30 min. The mixture is cooled again to −78° C. and methyl iodide (2.3 mL, 36.9 mmol) is added. The mixture is then warmed to RT over 1 h. NH4Cl solution is added and extracted with EtOAc. The organic extract is dried with MgSO4, concentrated and purified by chromatography to give the title compound (2.38 g): (M+H)+=177.

後処理

  1. temperaturethe mixture is warmed to 10° C. for 30 min
  2. temperatureThe mixture is cooled again to −78° C.
  3. temperatureThe mixture is then warmed to RT over 1 h
  4. extractionextracted with EtOAc
  5. extractionThe organic extract
  6. dry with materialis dried with MgSO4
  7. concentrationconcentrated
  8. custompurified by chromatography

出典と根拠

ORDレコード
ord-fd0cd4ccf53c4c05b64e2e0a30f64b4f
出典データセット
uspto-grants-2010_04
特許番号
US07700633B2

関連ノート

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