Ethanol → 4-(5-Ethoxymethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one

HRID 1690739ノート

反応式

HRID 1690739 の反応式
Cl[CH2:2][C:3]1[N:7]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[O:10][C:9]2([CH3:20])[CH3:19])[CH:6]=[N:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[CH2:30]([OH:32])[CH3:31]>>[CH2:30]([O:32][CH2:2][C:3]1[N:7]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[O:10][C:9]2([CH3:20])[CH3:19])[CH:6]=[N:5][CH:4]=1)[CH3:31]

参加物

4

反応物 3

HCID 702EthanolHCID 81531DiisopropylethylamineHCID 669066914-(5-Chloromethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one

生成物 1

HCID 577810774-(5-Ethoxymethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one

実験手順

To a solution of 4-(5-chloromethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one (0.150 g, 0.516 mmol), prepared as described in Example 18, in anhydrous ethanol (5 mL) is added diisopropylethyl amine (0.100 g, 0.77 mmol) and the mixture is stirred at reflux overnight. The mixture is purified by semi-preparative reverse phase HPLC to give 4-(5-ethoxymethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one as a white solid; MS (ESI) m/z 301.0 (M+H); 1H NMR (400 MHz, MeOD) δ ppm 1.26 (s, 3 H), 1.29 (t, J=6.1 Hz, 3 H), 1.54 (s, 3 H), 3.62 (br. s, 2 H), 4.70 (br. s, 2 H), 5.59 (s, 1 H), 7.02 (s, 1 H), 7.29 (br. s, 1 H), 7.52 (d, J=7.8 Hz, 1 H), 7.63 (td, J=7.8, 1.3 Hz, 1 H), 7.74 (td, J=7.6, 1.3 Hz, 1 H), 8.21 (dd, J=7.8, 1.3 Hz, 1H).

後処理

  1. temperatureat reflux overnight
  2. customThe mixture is purified by semi-preparative reverse phase HPLC

出典と根拠

ORDレコード
ord-be7afdd112e14dc99f6147ddb0ea255c
出典データセット
uspto-grants-2012_04
特許番号
US08153674B2

反応ノート

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