Hexane → HCID 58193579, compound

HRID 1922551Notes

Reaction equation

HRID 1922551 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-93c5182a91164bbd89ed3ad2ba87ea8f
Source dataset
uspto-grants-2012_05
Patent number
US08173749B2

Reaction notes

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