Dimethylformamide → HCID 22664977, compound

HRID 392590Notes

Reaction equation

HRID 392590 reaction equation
CN(C)C=O.[C:6]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.I[CH2:21][CH2:22][CH2:23][CH2:24]I.C(=O)([O-])[O-].[Na+].[Na+]>O>[OH:13][CH:6]([C:14]1([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:24][CH2:23][CH2:22][CH2:21]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7170Ethyl benzoylacetateHCID 10340Sodium CarbonateHCID 123371,4-Diiodobutane

Product 1

HCID 22664977HCID 22664977, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To N,N-dimethylformamide (400 ml) were added ethyl benzoylacetate (25.1 g, 0.13 mol), 1,4-diiodobutane (40.47 g) (0.13 g) and anhydrous sodium carbonate (82.7 g, 0.78 mol) and the mixture was stirred at 60° C. for 15.5 h. The reaction mixture was poured into 1 L of water and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dehydrated over anhydrous sodium sulfate and concentrated. A red residual solution (33.5 g) was purified by silica gel column chromatography (ethyl acetate/hexane=1/4) to give the title compound (24.67 g) as a colorless oil (yield 77%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. concentrationconcentrated
  4. customA red residual solution (33.5 g) was purified by silica gel column chromatography (ethyl acetate/hexane=1/4)

Sources & evidence

ORD record
ord-c7cc2e86e5eb4e9fa840a369eac07b6b
Source dataset
uspto-grants-2004_10
Patent number
US06800778B1

Reaction notes

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