HCID 59381262, compound → HCID 59381261, compound

HRID 2090144Notes

Reaction equation

HRID 2090144 reaction equation
[CH3:1][O:2][C:3](=[O:69])/[CH:4]=[CH:5]/[C:6]1[CH:68]=[CH:67][C:9]([C:10]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20](=[O:66])[C:21]([CH2:56][C:57]2[CH:62]=[CH:61][C:60]([N+:63]([O-])=O)=[CH:59][CH:58]=2)([CH2:46][C:47]2[CH:52]=[CH:51][C:50]([N+:53]([O-])=O)=[CH:49][CH:48]=2)[C:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][O:31][C:32](=[O:45])[C:33]2[CH:38]=[CH:37][C:36](/[CH:39]=[CH:40]/[C:41]([O:43][CH3:44])=[O:42])=[CH:35][CH:34]=2)=[O:23])=[O:11])=[CH:8][CH:7]=1>CN(C)C=O.O.[Zn]>[CH3:1][O:2][C:3](=[O:69])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[CH:8][C:9]([C:10]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20](=[O:66])[C:21]([CH2:56][C:57]2[CH:62]=[CH:61][C:60]([NH2:63])=[CH:59][CH:58]=2)([CH2:46][C:47]2[CH:52]=[CH:51][C:50]([NH2:53])=[CH:49][CH:48]=2)[C:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][O:31][C:32](=[O:45])[C:33]2[CH:38]=[CH:37][C:36](/[CH:39]=[CH:40]/[C:41]([O:43][CH3:44])=[O:42])=[CH:35][CH:34]=2)=[O:23])=[O:11])=[CH:67][CH:68]=1

Participants

5

Reactant 1

HCID 59381262HCID 59381262, compound

Product 1

HCID 59381261HCID 59381261, compoundYield 64.4%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1.30 g (1.36 mmol) bis[6-({4-[(1E)-3-methoxy-3-oxoprop-1-enyl]benzoyl}oxy)-hexyl]2,2 bis(4-nitrobenzyl)malonate were dissolved in a mixture of 25 ml N,N-dimethylformamide and 2.8 ml water. 2.21 g (8.18 mmol) ferric chloride hexahydrate and 0.716 g (10.95 mmol) Zinc powder were added, the temperature rise to 40° C. The mixture was allowed to react for 1 hours. The black reaction mixture was then partitioned between ethyl acetate and water and filtered. The organic phase was washed repeatedly with water, dried over sodium sulfate, filtered and concentrated by rotary evaporation. A first chromatography on 50 g silica gel using tert-butyl methyl ether as eluant and a second chromatography on 25 g silica gel using toluene: ethyl acetate (9:1) then (4:1) as eluant yielded 0.78 g (64%) of bis[6-({4-[(1E)-3-methoxy-3-oxoprop-1-enyl]benzoyl}oxy)hexyl]2,2 bis(4-aminobenzyl)malonate as a yellow powder.

Workup

  1. customto 40° C
  2. customto react for 1 hours
  3. customThe black reaction mixture
  4. customwas then partitioned between ethyl acetate and water
  5. filtrationfiltered
  6. washThe organic phase was washed repeatedly with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-fd3d5a6790bf46d1830aee14ccb36309
Source dataset
uspto-grants-2013_05
Patent number
US08436132B2

Reaction notes

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