Hydrochloric Acid → Dimethyl (4-methoxy-2-nitrobenzyl)malonate

HRID 2269724Notes

Reaction equation

HRID 2269724 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[C:12]([C:17]([O:19][CH3:20])=[O:18])[C:13]([O:15][CH3:16])=[O:14])=[C:7]([N+:21]([O-:23])=[O:22])[CH:6]=1.Cl>CO>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([C:13]([O:15][CH3:16])=[O:14])[C:17]([O:19][CH3:20])=[O:18])=[C:7]([N+:21]([O-:23])=[O:22])[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 54325413Dimethyl (4-methoxy-2-nitrophenyl)methylidenemalonate

Product 1

HCID 53955072Dimethyl (4-methoxy-2-nitrobenzyl)malonateYield 75.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (3.36 g) was added to a methanol (200 ml) solution of dimethyl (4-methoxy-2-nitrophenyl)methylidenemalonate (25 g) under ice-cooling. The reaction mixture was stirred at room temperature for one hour and then neutralized by adding dropwise 1N aqueous hydrochloric acid solution. The reaction mixture was concentrated and extracted with ethyl acetate. The organic layer was washed with water, a saturated aqueous potassium bicarbonate solution and a saturated aqueous sodium chloride solution, then dried and concentrated. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/4) to obtain the entitled compound (19 g).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous potassium bicarbonate solution and a saturated aqueous sodium chloride solution, then dried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/4)

Sources & evidence

ORD record
ord-8acfaa4e04714efea2c6522adb54d879
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

Loading…