Diethyl Ether → Methyl 2-methoxy-5-(t-butyldimethylsilyloxy)benzoate

HRID 637218ノート

反応式

HRID 637218 の反応式
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:20](=O)([O-])[O-].[K+].[K+].CI.C(OCC)C>CC(C)=O.C(OCC)(=O)C.CCCCCC>[CH3:20][O:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 6328Methyl iodide2 回HCID 11430Potassium CarbonateHCID 18465044Methyl 5-((tert-butyldimethylsilyl)oxy)-2-hydroxybenzoate

生成物 1

HCID 18464864Methyl 2-methoxy-5-(t-butyldimethylsilyloxy)benzoate

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 21226206Ethyl acetate hexane溶媒

実験手順

Combine methyl 2-hydroxy-5-(t-butyldimethylsilyloxy)benzoate (14.2 g, 50.2 mmol), potassium carbonate (13.88 g, 100.4 mmol), and methyl iodide (20 mL, 321 mmol) in acetone (125 mL). Heat to reflux. After 17 hours, add methyl iodide (10 mL). After 23 hours, cool the reaction mixture to ambient temperature and add diethyl ether (600 mL), filter, and evaporate the filtrate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 10% ethyl acetate/hexane to give methyl 2-methoxy-5-(t-butyldimethylsilyloxy)benzoate. Rf=0.39 (silica gel, 5% ethyl acetate/hexane).

後処理

  1. temperatureHeat to reflux
  2. waitAfter 23 hours
  3. filtrationfilter
  4. customevaporate the filtrate in vacuo
  5. customto give a residue

出典と根拠

ORDレコード
ord-ddf336ee2fbf4b0186213eae28b14c53
出典データセット
uspto-grants-2001_02
特許番号
US06194406B1

反応ノート

読み込み中…