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

HRID 2230680Notes

Reaction equation

HRID 2230680 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-9ded7963a0b646b2a2647fc38d708dee
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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