Ethyl Acetate → HCID 86625099, compound

HRID 1922556Notes

Reaction equation

HRID 1922556 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:44]=[C:45]([N+:82]([O-])=O)[C:46]=1[O:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][O:54][C:55](=[O:81])/[CH:56]=[CH:57]/[C:58]1[CH:63]=[CH:62][C:61]([O:64][C:65](=[O:80])[C:66]2[CH:71]=[CH:70][C:69]([O:72][CH2:73][CH2:74][CH2:75][C:76]([F:79])([F:78])[F:77])=[CH:68][CH:67]=2)=[CH:60][CH:59]=1)[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17](=[O:43])/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27](=[O:42])[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37][C:38]([F:41])([F:40])[F:39])=[CH:30][CH:29]=2)=[CH:22][CH:21]=1)=[O:8])([O-])=O.C(OCC)(=O)C>CN(C)C=O.O.[Zn]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:44]=[C:45]([NH2:82])[C:46]=1[O:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][O:54][C:55](=[O:81])/[CH:56]=[CH:57]/[C:58]1[CH:63]=[CH:62][C:61]([O:64][C:65](=[O:80])[C:66]2[CH:71]=[CH:70][C:69]([O:72][CH2:73][CH2:74][CH2:75][C:76]([F:77])([F:78])[F:79])=[CH:68][CH:67]=2)=[CH:60][CH:59]=1)[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17](=[O:43])/[CH:18]=[CH:19]/[C:20]1[CH:21]=[CH:22][C:23]([O:26][C:27](=[O:42])[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37][C:38]([F:40])([F:39])[F:41])=[CH:30][CH:29]=2)=[CH:24][CH:25]=1)=[O:8]

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 86625100HCID 86625100, compound

Product 1

HCID 86625099HCID 86625099, compoundYield 0.1%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

7.70 g (6.5 mol) of 6-{[((2E)-3-{4-[(4-(4,4,4-trifluorobutoxy)benzoyl)oxy]phenyl}prop-2-enoyl)oxy]}hexyl 3,5-dinitro-4-[6-{[((2E)-3-{4-[(4-(4,4,4-trifluorobutoxy)benzoyl) oxy]phenyl}prop-2-enoyl)oxy]}hexyloxy]benzoate are dissolved in a mixture of 90 ml of N,N-dimethylformamide and 7 ml water. 10.6 g (39.2 mmol) ferric chloride hexahydrate are added. 4.27 g (65.36 mmol) Zinc powder are added portionwise within 40 min. The mixture is allowed to react for 2 hours. The reaction mixture is then partitioned between ethyl acetate and water and filtered. The organic phase is washed repeatedly with water, dried over sodium sulfate, filtered and concentrated by rotary evaporation. Chromatography of the residue on 200 g silica gel using toluene:ethyl acetate 2:1 as eluant and crystallization form methanol:ethyl acetate mixture to yield 4.92 g 6-{[((2E)-3-{4-[(4-(4,4,4-trifluorobutoxy)benzoyl)oxy]phenyl}prop-2-enoyl)oxy]}hexyl 3,5-Diamino-4-[6-{[((2E)-3-{4-[(4-(4,4,4-trifluorobutoxy)benzoyl)oxy]phenyl}prop-2-enoyl)oxy]}hexyloxy]benzoate as colorless crystals.

Workup

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

Sources & evidence

ORD record
ord-756adb5732b8429c8f54353128105135
Source dataset
uspto-grants-2012_05
Patent number
US08173749B2

Reaction notes

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