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

HRID 2230680ノート

反応式

HRID 2230680 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-9ded7963a0b646b2a2647fc38d708dee
出典データセット
uspto-grants-2002_07
特許番号
US06423704B1

反応ノート

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