Methyl Acetate → HCID 67417683, compound

HRID 1627059Notes

Reaction equation

HRID 1627059 reaction equation
Br[C:2]1[C:10]2[O:11][CH2:12][CH2:13][C:9]=2[C:8]2[C@H:7]([CH2:14][CH2:15][NH:16][C:17](=[O:20])[CH2:18][CH3:19])[CH2:6][CH2:5][C:4]=2[CH:3]=1.[C:21](OC)(=[O:23])C>[Cu]Br.C[O-].[Na+]>[CH3:21][O:23][C:2]1[C:10]2[O:11][CH2:12][CH2:13][C:9]=2[C:8]2[C@H:7]([CH2:14][CH2:15][NH:16][C:17](=[O:20])[CH2:18][CH3:19])[CH2:6][CH2:5][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 6584Methyl AcetateHCID 58435488(S)-N-(2-[4-bromo-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl)propionamide

Product 1

HCID 67417683HCID 67417683, compoundYield 60.2%

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 10942334Sodium MethoxideSolvent

Procedure

A solution of sodium methoxide (200 mL, 28% solution in methanol) was added dropwise into a mixture of (S)—N-(2-[4-bromo-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl)propionamide (5.00 g, 14.8 mmol), copper(I) bromide (2.12 g, 14.8 mmol) and methyl acetate (3.29 g, 44.3 mmol). The mixture was refluxed for 5 hours. The mixture was cooled, which was quenched with 1N HCl, followed by extracting with methanol-chloroform. The extracted solution was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of silica gel column chromatography and recrystallized from ethyl acetate to afford the title compound (yield 2.58 g, 60%) as a white powder.

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. temperatureThe mixture was cooled
  3. customwhich was quenched with 1N HCl
  4. extractionby extracting with methanol-chloroform
  5. dry with materialThe extracted solution was dried over anhydrous magnesium sulfate
  6. distillationby distilling off the solvent under reduced pressure
  7. customThe residue was purified by means of silica gel column chromatography
  8. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-48d5f18ac1434ffdbb1b943528707bba
Source dataset
uspto-grants-2014_07
Patent number
US08785491B2

Reaction notes

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