Hexane → HCID 58193579, compound

HRID 2193511Notes

Reaction equation

HRID 2193511 reaction equation
[F:1][C:2]([F:31])([C:27]([F:30])([F:29])[F:28])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:26]=[CH:25][C:10]([C:11]([O:13][C:14]2[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22]([O-:24])=[O:23])=[CH:16][CH:15]=2)=[O:12])=[CH:9][CH:8]=1.CCCCCC.FC(F)(F)CCCOC1C=CC(C(OC2C=CC(/C=C/C(O[CH2:62][CH2:63][C:64]3[CH:69]=[CH:68][C:67]([NH2:70])=[CH:66][C:65]=3[NH2:71])=O)=CC=2)=O)=CC=1>CN(C)C=O.O.[Zn]>[F:1][C:2]([F:31])([C:27]([F:28])([F:29])[F:30])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:26]=[CH:25][C:10]([C:11]([O:13][C:14]2[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22]([O:24][CH2:62][CH2:63][C:64]3[CH:69]=[CH:68][C:67]([NH2:70])=[CH:66][C:65]=3[NH2:71])=[O:23])=[CH:16][CH:15]=2)=[O:12])=[CH:9][CH:8]=1

Participants

7

Reactant 3

HCID 8058HexaneHCID 59850421HCID 59850421, compoundHCID 86625096HCID 86625096, compound

Product 1

HCID 58193579HCID 58193579, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5.35 g (8.38 mmol) of (2E)3-{4-[(4-(4,4,5,5,5-pentafluoropentoxy)benzoyl)oxy]phenyl}acrylate are dissolved in a mixture of 54 ml of N,N-dimethylformamide and 6 ml water. 13.9 g (51.4 mmol) ferric chloride hexahydrate are added. 5.60 g (85.7 mmol) Zinc powder are added portionwise within 60 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. Filtration of the residue on 200 g silica gel using toluene:ethyl acetate (1:3) as eluant and crystallization form ethylacetate:hexane mixture yielded 3.30 g 2-(2,4-Diaminophenyl)ethyl (2E)3-{4-[(4-(4,4,5,5,5-pentafluoropentoxy)benzoyl)oxy]phenyl}acrylate as yellowish crystals 2-(2,4-Diaminophenyl)ethyl (2E)3-{4-[(4-(4,4,4-trifluorobutoxy)benzoyl)oxy]phenyl}acrylate is prepared analogous to example 4 using (2E)-3-(4-{[4-(4,4,4-trifluorobutoxy)benzoyl]oxy}phenyl)acrylic acid.

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. filtrationFiltration of the residue on 200 g silica gel
  9. customcrystallization
  10. customform ethylacetate

Sources & evidence

ORD record
ord-c6d318a407c04282aacc7c6c03daf274
Source dataset
uspto-grants-2012_12
Patent number
US08329823B2

Reaction notes

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