Hexane → HCID 86625097, compound

HRID 1042619Notes

Reaction equation

HRID 1042619 reaction equation
[N+:1]([C:4]1[CH:79]=[CH:78][C:7]([CH2:8][C:9]([CH2:68][C:69]2[CH:74]=[CH:73][C:72]([N+:75]([O-])=O)=[CH:71][CH:70]=2)([CH2:40][C:41](=[O:67])/[CH:42]=[CH:43]/[C:44]2[CH:49]=[CH:48][C:47]([O:50][C:51](=[O:66])[C:52]3[CH:57]=[CH:56][C:55]([O:58][CH2:59][CH2:60][CH2:61][C:62]([F:65])([F:64])[F:63])=[CH:54][CH:53]=3)=[CH:46][CH:45]=2)[C:10]([C:13](=[O:39])/[CH:14]=[CH:15]/[C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23](=[O:38])[C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][CH2:33][C:34]([F:37])([F:36])[F:35])=[CH:26][CH:25]=3)=[CH:18][CH:17]=2)([OH:12])[OH:11])=[CH:6][CH:5]=1)([O-])=O.CCCCCC>CN(C)C=O.O.[Zn]>[NH2:75][C:72]1[CH:73]=[CH:74][C:69]([CH2:68][C:9]([CH2:8][C:7]2[CH:78]=[CH:79][C:4]([NH2:1])=[CH:5][CH:6]=2)([CH2:40][C:41](=[O:67])/[CH:42]=[CH:43]/[C:44]2[CH:49]=[CH:48][C:47]([O:50][C:51](=[O:66])[C:52]3[CH:57]=[CH:56][C:55]([O:58][CH2:59][CH2:60][CH2:61][C:62]([F:63])([F:64])[F:65])=[CH:54][CH:53]=3)=[CH:46][CH:45]=2)[C:10]([C:13](=[O:39])/[CH:14]=[CH:15]/[C:16]2[CH:17]=[CH:18][C:19]([O:22][C:23](=[O:38])[C:24]3[CH:25]=[CH:26][C:27]([O:30][CH2:31][CH2:32][CH2:33][C:34]([F:37])([F:36])[F:35])=[CH:28][CH:29]=3)=[CH:20][CH:21]=2)([OH:11])[OH:12])=[CH:70][CH:71]=1

Participants

6

Reactant 2

HCID 8058HexaneHCID 86625098HCID 86625098, compound

Product 1

HCID 86625097HCID 86625097, compoundYield 0.1%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2.20 g (2.00 mol) of 2,2-bis(4-nitrobenzyl)-1,3di[(2E)-3-{4-[(4-(4,4,4-trifluorobutoxy)benzoyl)oxy]phenyl}prop-2-enoyl]propanediol are dissolved in a mixture of 25 ml of N,N-dimethylformamide and 3 ml water. 3.25 g (12.01 mmol) ferric chloride hexahydrate are added. 1.31 g (20.02 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 100 g silica gel using toluene:ethyl acetate 1:1 as eluant and crystallization form ethylacetate:hexane mixture to yield 1.20 g 2,2-bis(4-aminobenzyl)-1,3di[(2E)-3-{4-[(4-(4,4,4-trifluorobutoxy)benzoyl)oxy]phenyl}prop-2-enoyl]propanediol

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 ethylacetate

Sources & evidence

ORD record
ord-f39a22e7dfbc4c99b1bc3da0c089f18e
Source dataset
uspto-grants-2013_10
Patent number
US08557922B2

Reaction notes

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