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Sodium hydride → Ethyl 5-benzyloxy-1-(2-chloro-4,5-methylenedioxybenzyl)indole-2-carboxylate

HRID 618753
ノート
印刷プレビュー

反応式

HRID 618753 の反応式
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:25]1[O:29][C:28]2[CH:30]=[C:31]([Cl:36])[C:32]([CH2:34]Cl)=[CH:33][C:27]=2[O:26]1>CN(C=O)C>[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:34][C:32]1[CH:33]=[C:27]3[O:26][CH2:25][O:29][C:28]3=[CH:30][C:31]=1[Cl:36])[C:15]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:14]2)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1
参加物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 24758Sodium hydrideHCID 901136-Chloropiperonyl chlorideHCID 95721Ethyl 5-(phenylmethoxy)-1H-indole-2-carboxylate

生成物 1

HCID 15433189Ethyl 5-benzyloxy-1-(2-chloro-4,5-methylenedioxybenzyl)indole-2-carboxylate収率 50%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirring suspension of sodium hydride (2.03grams (hereinafter "g"), (60% in mineral oil), 50.8 millimoles (hereinafter "mmol")) in DMF (100 milliliters (hereinafter "mL")) was added ethyl 5-benzyloxyindole-2-carboxylate (10.0 g, 33.9 mmol). After 10 minutes (hereinafter "min"), 6-chloropiperonyl chloride (10.4 g, 50.8 mmol) was added. After 1 hour, the mixture was partitioned between water and ethyl acetate. The organic layer was washed with water and saturated brine, dried (MgSO4), filtered and concentrated to leave an oily pale yellow solid. The solid was recrystallized from ethanol to provide the title compound as a white solid (7.8 g, 50%). 1HNMR (400 MHz, CDCl3) d 7.49-7.33 (m, 6H), 7.19-7.08 (m, 3H), 6.87 (s, 1H), 5.86 (s, 2H), 5.78 (s, 1H), 5.77 (s, 2H), 5.11 (s, 2H), 4.33 (q, 2H), 1.36 (t, 3H).

後処理

  1. customthe mixture was partitioned between water and ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto leave an oily pale yellow solid
  7. customThe solid was recrystallized from ethanol

出典と根拠

ORDレコード
ord-2a19717096534eaabe645841464d90bb
出典データセット
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05955492

反応ノート

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