Ethanol → 3-Ethyl-4,6-dihydroxy-2-(methoxycarbonylmethyl)benzoic acid methyl ester

HRID 505667ノート

反応式

HRID 505667 の反応式
[CH3:1][O:2][C:3](=[O:11])[CH:4]=[C:5]=[CH:6][C:7]([O:9][CH3:10])=[O:8].C([O:14][C:15](O[Si](C)(C)C)=[CH:16][C:17]([O:21][Si](C)(C)C)=[CH:18][CH2:19][CH3:20])C.C(O)C.[F-].[NH4+]>O>[CH3:10][O:9][C:7](=[O:8])[C:6]1[C:15]([OH:14])=[CH:16][C:17]([OH:21])=[C:18]([CH2:19][CH3:20])[C:5]=1[CH2:4][C:3]([O:2][CH3:1])=[O:11]

参加物

6

反応物 4

HCID 702EthanolHCID 25516Ammonium fluorideHCID 637810Dimethyl penta-2,3-dienedioateHCID 729526991-Ethoxy-1,3-bis(trimethylsiloxy)hexa-1,3-diene

生成物 1

HCID 115363173-Ethyl-4,6-dihydroxy-2-(methoxycarbonylmethyl)benzoic acid methyl ester収率 40%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

The above-obtained penta-2,3-dienedioic acid dimethyl ester (4.6 g, 30 mmol) and 1-ethoxy-1,3-bis(trimethylsiloxy)hexa-1,3-diene (13 g, 41 mmol) were mixed and stirred at a room temperature for 1.5 hours. The reaction mixture was added with ethanol (100 mL) and ammonium fluoride (5.4 g) and stirred at a room temperature for 2 hours. The reaction mixture was further added with water and extracted with ethyl acetate 3 times. The organic layers were combined, sequentially washed with water and saturated brine, dried over anhydrous sodium sulfate and then the solvent was evaporated under reduced pressure. The residue was triturated with hexane (50 mL) to obtain Compound 23 (3.2 g, 40%).

後処理

  1. stirringstirred at a room temperature for 2 hours
  2. extractionextracted with ethyl acetate 3 times
  3. washsequentially washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was triturated with hexane (50 mL)

出典と根拠

ORDレコード
ord-8da847751b78430b91614233e4d53ef2
出典データセット
uspto-grants-2010_08
特許番号
US07781485B2

反応ノート

読み込み中…