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

HRID 382961Notes

Reaction equation

HRID 382961 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-4963f30420074ae3a66fcd7f324466f6
Source dataset
uspto-grants-2001_10
Patent number
US06310107B1

Reaction notes

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