Acetone → HCID 86677538, compound

HRID 335056Notes

Reaction equation

HRID 335056 reaction equation
[CH2:1]1[CH2:5][O:4][CH2:3][CH2:2]1.[CH3:6][C:7]([CH3:9])=O.[OH2:10].I([O-])(=O)(=O)=O.[Na+].[C:17]([O:20][CH2:21]C)(=[O:19])[CH3:18]>[Os](=O)(=O)(=O)=O>[CH:6]([C:7]1[C:2]2[C:1](=[CH:5][CH:1]=[CH:2][CH:3]=2)[C:5]([O:4][CH3:3])=[C:18]([C:17]([O:20][CH3:21])=[O:19])[CH:9]=1)=[O:10]

Participants

7

Reactant 5

HCID 180AcetoneHCID 962WaterHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 23667635Sodium periodate

Product 1

HCID 86677538HCID 86677538, compound

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

To a solution of the above compound (4.10 g, 16.9 mmol) in a 200 mL of a 2:1:1 mixture of THF:acetone:water was added sodium periodate (10.9 g, 50.8 mmol) and osmium tetroxide (4% aqueous solution, 6.65 mL, 0.847 mmol) dropwise. After 2 hours, the reaction was diluted with ethyl acetate, washed with water, aqueous sodium thiosulfate, and brine. The organic solution was dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-20% ethyl acetate in hexanes to provide methyl 4-formyl-1-methoxy-2-naphthoate that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 245.2 for [M+H]+.

Workup

  1. washwashed with water, aqueous sodium thiosulfate, and brine
  2. dry with materialThe organic solution was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified via silica gel chromatography
  6. washeluting with 0-20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b3698e6a113742319f1f440b8bf50333
Source dataset
uspto-grants-2014_11
Patent number
US08883850B2

Reaction notes

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