Methyl iodide → 3-Oxo-2-oxa-bicyclo[2.2.1]heptane-5-carboxylic acid methyl ester

HRID 2242427Notes

Reaction equation

HRID 2242427 reaction equation
[O:1]=[C:2]1[CH:7]2[CH2:8][CH:4]([CH2:5][CH:6]2[C:9]([OH:11])=[O:10])[O:3]1.[CH3:12]I>CC(C)=O.[Ag-]=O>[CH3:12][O:10][C:9]([CH:6]1[CH2:5][CH:4]2[CH2:8][CH:7]1[C:2](=[O:1])[O:3]2)=[O:11]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 462449653-Oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acid

Product 1

HCID 592041763-Oxo-2-oxa-bicyclo[2.2.1]heptane-5-carboxylic acid methyl esterYield 64%

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 180AcetoneSolvent

Procedure

Compound 32 (1.014 g, 6.50 mmol) was dissolved in acetone (35 mL) before methyl iodide (13.68 g, 96.4 mmol) and silver (I) oxide (1.61 g, 6.95 mmol) were added. After stirring for 3 h the mixture was filtered through celite and the filtrate was evaporated before purification by flash column chromatography (toluene/ethyl acetate 4:1) was performed yielding the methyl ester 41 (702 mg, 64%) as white crystals.

Workup

  1. additionwere added
  2. filtrationwas filtered through celite
  3. customthe filtrate was evaporated before purification by flash column chromatography (toluene/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-60fa8fe8bec5456ea6cef8f3bc60f353
Source dataset
uspto-grants-2010_03
Patent number
US07671032B2

Reaction notes

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