1-Chloro-4-(chloromethyl)benzene → Ethyl 1-(4-chlorobenzyl)-1H-indole-2-carboxylate

HRID 2305579ノート

反応式

HRID 2305579 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[H-].[Na+].[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Cl)=[CH:20][CH:19]=1>CN(C=O)C>[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[C:2]2[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:20][CH:19]=1

参加物

5

反応物 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 73125Ethyl indole-2-carboxylate

生成物 1

HCID 10519288Ethyl 1-(4-chlorobenzyl)-1H-indole-2-carboxylate収率 74%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Ethyl indole-2-carboxylate (0.5 g) was dissolved in DMF and sodium hydride (0.116 g) was added in a single portion. The reaction was stirred for 1 hour, then 4-chlorobenzyl chloride (0.468 g) was added dropwise. Stirring was continued for a further 2 hours and then the reaction was quenched by the addition of water. The reaction mixture was partitioned between water and ethyl acetate. Combined organic extracts were dried (MgSO4) and concentrated in vacuo and the residue purified by column chromatography using isohexane-5% ethyl acetate as eluent to give the desired end product as a white solid (0.61 g, 74%), mp 107-108°; NMR δ(CD3SOCD3) 1.25 (t, 3H), 4.3 (q, 2H), 5.8 (s, 2H), 7.1 (t, 1H), 7.3 (m, 4H), 7.55 (d, 1H), 7.7 (d, 1H); M/z (+) 314 (MH+).

後処理

  1. stirringStirring
  2. waitwas continued for a further 2 hours
  3. customthe reaction was quenched by the addition of water
  4. customThe reaction mixture was partitioned between water and ethyl acetate
  5. dry with materialCombined organic extracts were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customthe residue purified by column chromatography

出典と根拠

ORDレコード
ord-1ef09978b6334387952d4a877ca9d5b8
出典データセット
uspto-grants-2002_08
特許番号
US06441004B1

反応ノート

読み込み中…