Ethyl Acetate → HCID 21071406、化合物

HRID 1371913ノート

反応式

HRID 1371913 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:6]=[C:5]2[CH2:21][CH2:22][N:23]1[C:31](=[O:32])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]1=[O:33].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:41][CH2:42][CH3:43].CCOC(C)=O>CN(C=O)C>[CH2:41]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([Si:11]([CH:12]([CH3:14])[CH3:13])([CH:18]([CH3:19])[CH3:20])[CH:15]([CH3:16])[CH3:17])[CH:6]=[C:5]2[CH2:21][CH2:22][N:23]1[C:24](=[O:33])[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:31]1=[O:32])[CH2:42][CH3:43]

参加物

6

反応物 4

HCID 8857Ethyl Acetate2 回HCID 10796Cesium carbonateHCID 336431-IodopropaneHCID 21071403HCID 21071403、化合物

生成物 1

HCID 21071406HCID 21071406、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Combine 2-(2-(5-hydroxy-1-triisopropylsilanyl-1H-indol-3-yl)ethyl)isoindole-1,3-dione (0.7 g, 1.5 mmol), cesium carbonate (1 g, 3 mmol) and 1-iodopropane (0.4 g, 2.3 mmol) in DMF (25 mL) and stir at ambient temperature overnight. Pour the reaction mixture into 50% EtOAc in hexanes and wash three times with brine. Dry the organic layer over MgSO4 and concentrate under vacuum to give an oil. Chromatograph the oil on silica gel eluting with 5% EtOAc in hexanes to give the title compound: ISMS 505 (M+1); 1H NMR (CDCl3) 7.80–7.78 (m, 2H), 7.67–7.65 (m, 2H), 7.30–7.27 (d, 1H), 7.12–7.11 (d, 1H), 7.02 (s, 1H), 6.77–6.74 (m, 1H), 4.01–3.96 (m, 4H), 3.12–3.08 (m; 2H), 1.86–1.81 (m 2H), 1.64–1.57 (m, 3H), 1.08–1.04 (m, 21H).

後処理

  1. washwash three times with brine
  2. dry with materialDry the organic layer over MgSO4
  3. concentrationconcentrate under vacuum
  4. customto give an oil

出典と根拠

ORDレコード
ord-9eea7b9884e047889154b63f7c277ea1
出典データセット
uspto-grants-2007_01
特許番号
US07157488B2

反応ノート

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