Methyl iodide → ethyl 1-methyl-1H-indole-2-carboxylate

HRID 225835

反応式

HRID 225835 の反応式
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]1[C:12]([O:14][CH2:15][CH3:16])=[O:13].[CH3:17]I>CN(C=O)C>[CH3:17][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 73125Ethyl indole-2-carboxylate

生成物 1

HCID 143368ethyl 1-methyl-1H-indole-2-carboxylate収率 99.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

NaH (60% dispersion in mineral oil, 8.02 g, 200.49 mmole) was washed with hexanes, then was suspended in dry DMF (530 mL). Solid ethyl indole-2-carboxylate (25.29 g, 133.66 mmole) was added portionwise over 5-10 min, allowing gas evolution to subside between additions. When the addition was complete, the yellow mixture was stirred for 15 min, then methyl iodide (42 mL, 668.3 mmole) was added all at once. The reaction was exothermic, and the internal temperature rose to 40-45° C. After 1 hr, the reaction was quenched with 10% NH4Cl (100 mL) and concentrated on the rotavap (high vacuum). The residue was partitioned between Et2O(500 mL) and H2O (100 mL), and the layers were separated. The Et2O layer was washed with H2O (100 mL), dried (MgSO4), and concentrated to leave the title compound (27.10 g, quantitative) as a light yellow solid. This was used without further purification: TLC (10% EtOAc/hexanes) Rf=0.39.

後処理

  1. additionWhen the addition
  2. customrose to 40-45° C
  3. waitAfter 1 hr
  4. customthe reaction was quenched with 10% NH4Cl (100 mL)
  5. concentrationconcentrated on the rotavap (high vacuum)
  6. customThe residue was partitioned between Et2O(500 mL) and H2O (100 mL)
  7. customthe layers were separated
  8. washThe Et2O layer was washed with H2O (100 mL)
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-2d32ed043a944ab38cc8667bfc89e046
出典データセット
uspto-grants-2009_07
特許番号
US07557125B2

関連ノート

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