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

HRID 854033Notes

Reaction equation

HRID 854033 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[C:10]([C:15]([O:17][CH3:18])=[O:16])[C:11]([O:13][CH3:14])=[O:12])=[C:5]([N+:19]([O-:21])=[O:20])[CH:4]=1.[BH4-].[Na+].Cl>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([C:11]([O:13][CH3:14])=[O:12])[C:15]([O:17][CH3:18])=[O:16])=[C:5]([N+:19]([O-:21])=[O:20])[CH:4]=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

To a solution of dimethyl (4-methoxy-2-nitrophenyl)methylidenemalonate (25 g) in methanol (200 ml) was added sodium borohydride (3.36 g) in an ice bath. After stirring at room temperature for 1 hr, the reaction mixture was neutralized by adding 1 N aqueous hydrochloric acid. The reaction mixture was concentrated and extracted with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride, dried and concentrated. The residue was purified by silica gel column chromatography (eluent:ethyl acetate:hexane=1:4) to obtain the titled compound (19 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (eluent:ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-b226f661228c46af96603bf93b2d24d4
Source dataset
uspto-grants-2007_08
Patent number
US07256204B2

Reaction notes

Loading…