Sodium Hydroxide → 4-Benzyloxy-2-methyl-6-[3-(quinolin-2-ylmethoxy)-benzyloxy]-benzoic acid

HRID 892190ノート

反応式

HRID 892190 の反応式
[CH2:1]([O:8][C:9]1[CH:19]=[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH2:29][C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:31]=3)[CH:23]=2)[C:12]([C:13]([O:15]CC)=[O:14])=[C:11]([CH3:40])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH2:1]([O:8][C:9]1[CH:19]=[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH2:29][C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:31]=3)[CH:23]=2)[C:12]([C:13]([OH:15])=[O:14])=[C:11]([CH3:40])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 22241539Ethyl 4-benzyloxy-2-methyl-6-[3-(quinolin-2-ylmethoxy)-benzyloxy]-benzoate

生成物 1

HCID 222414744-Benzyloxy-2-methyl-6-[3-(quinolin-2-ylmethoxy)-benzyloxy]-benzoic acid

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Ethyl 4-benzyloxy-2-methyl-6-[3-(quinolin-2-ylmethoxy)-benzyloxy]-benzoate (2.4 g, 4.5 mmole, example 64) is added to ethanol (50 ml) and 11N sodium hydroxide (4.4 ml, 44 mmole) and refluxed for 8 hours. The solvent is removed in vacuo and the residue is dissolved in dichloromethane with a small amount of water and is acidified to pH6 with 1N HCl. The organic layer is dried over MgSO4 and the solvent removed in vacuo. The crude product is purified by column chromatography (silica, 1% methanol in dichloromethane) to provide the title compound. m.p. 146–149° C.; 1H NMR (300 MHz, CD3OD) d 8.34 (d, 1H), 8.04 (d, 1H), 7.91 (d, 1H), 7.78–7.70 (m, 2H), 7.61 (t, H), 7.37–7.20 (m, 7H), 7.05–6.91 (m, 2H), 6.51 (d, 1H), 6.47 (d, 1H), 5.35 (s, 2H), 5.09 (s, 2H), 5.03 (s, 2H), 2.29 (s, 3H); MS (ESI) 506 (M+H)+.

後処理

  1. temperaturerefluxed for 8 hours
  2. customThe solvent is removed in vacuo
  3. dissolutionthe residue is dissolved in dichloromethane with a small amount of water
  4. dry with materialThe organic layer is dried over MgSO4
  5. customthe solvent removed in vacuo
  6. customThe crude product is purified by column chromatography (silica, 1% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-1f8e1727dd384a27a364f2713ba2f2d8
出典データセット
uspto-grants-2006_02
特許番号
US07005440B1

反応ノート

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