Hydrochloric Acid → HCID 19698390, compound

HRID 862586Notes

Reaction equation

HRID 862586 reaction equation
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:14][C:15]1[CH:16]=[C:17]([C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=1)[CH:18]=[CH2:19].Cl>CN(C=O)C>[CH3:14][C:15]1[CH:16]=[C:17]([CH2:18][CH2:19][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10])[C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 21767387HCID 21767387, compound

Product 1

HCID 19698390HCID 19698390, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

To a suspension of 60% sodium hydride (1.36 g, 34 mmol) in DMF (35 mL) was added diethyl malonate (7.00 g, 43.7 mmol). The mixture was heated at 60° C. for 1.5 h, allowed to cool at room temperature and 3-methyl-6-nitrostyrene (4.80 g, 29.4 mmol) in DMF (10 mL) was added dropwise. The mixture was again heated at 4°~50° C. for 4 h, poured into 0.1N hydrochloric acid, and extracted with a 1:1 toluene/ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with 10:1 hexane/ethyl acetate to give 2.70 g of the title compound (28%).

Workup

  1. temperatureto cool at room temperature
  2. temperatureThe mixture was again heated at 4°~50° C. for 4 h
  3. extractionextracted with a 1:1 toluene/ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography with 10:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-e8d89aeb9c664d1aad7fb9c80a97b062
Source dataset
uspto-grants-1998_02
Patent number
US05719152

Reaction notes

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