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

HRID 637218노트

반응식

HRID 637218 반응식
[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]

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 6328Methyl iodide2회HCID 11430Potassium CarbonateHCID 18465044Methyl 5-((tert-butyldimethylsilyl)oxy)-2-hydroxybenzoate

생성물 1

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

시약·촉매·용매 2

HCID 180Acetone용매HCID 21226206Ethyl acetate hexane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-ddf336ee2fbf4b0186213eae28b14c53
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06194406B1

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