Acetic Acid → HCID 22931945, compound

HRID 1271246Notes

Reaction equation

HRID 1271246 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH2:7][CH2:8][C:9]2=O.[C:15]([BH3-])#[N:16].[Na+].C(O)(=O)C.O>C(O)C.CN>[CH3:15][NH:16][CH:9]1[C:10]2[C:6](=[C:5]([O:4][CH2:3][O:2][CH3:1])[CH:13]=[CH:12][CH:11]=2)[CH2:7][CH2:8]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 14139907HCID 14139907, compound

Product 1

HCID 22931945HCID 22931945, compoundYield 56.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6329MethylamineSolvent

Procedure

To a solution of 1.00 g of 4-(methoxymethoxy)-1-indanone in 10 ml of ethanol, 2.8 ml of 40% methylamine (methanol solution) and 367 mg of sodium cyanoborohydride were added. While stirring at room temperature, 0.55 ml of acetic acid was added dropwise and the mixture was heated at reflux for 4 hours. The reaction solution was air-cooled, combined with water and then extracted with ethyl acetate. After drying over anhydrous magnesium sulfate, the solvent was evaporated. The residue was purified by silica gel column chromatography to obtain 0.61 g of the desired compound as a deep green oily substance.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4 hours
  3. temperatureThe reaction solution was air-cooled
  4. extractionextracted with ethyl acetate
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-01c5d6db3c584a7ab9b40e3b9e3dfdc6
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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