Acetic Anhydride → 2-(4-(Ethylamino)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

HRID 854488Notes

Reaction equation

HRID 854488 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[CH3:18][C:19](OC(C)=O)=O>C1COCC1.N1C=CC=CC=1>[CH2:18]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:17])([C:9]([F:10])([F:11])[F:12])[C:13]([F:14])([F:15])[F:16])=[CH:6][CH:7]=1)[CH3:19]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 5778012-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 1

HCID 116663972-(4-(Ethylamino)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-olYield 96.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 1 g (3.86 mmol) of 2-(4-amino-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol in 2 ml of THF and 5 mL of pyridine was treated with 0.44 mL (4.63 mmol) of Ac2O and stirred for 2 hrs at 60° C. The solvent was evaporated and the crude distributed between a diluted aqueous solution of HCl and Et2O. the combined organic phases were dried over Na2SO4 and the solvent evaporated. The residue was dissolved in 5 mL of THF, treated with 7.7 mL of a 1M BH3*THF-solution in THF and refluxed for 2 hrs. The solvent was evaporated and the residue distributed between a diluted aqueous solution of NaOH and Et2O. The aqueous phase was then acidified by addition of an aqueous solution of HCl to a pH of ca. 7 and extracted with Et2O. The combined organic phases were dried over Na2SO4 and the solvent evaporated to give 1.07 g (96%) of crude 2-(4-ethylamino-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol, light yellow solid, MS: 288 (MH+).

Workup

  1. customThe solvent was evaporated
  2. dry with materialthe combined organic phases were dried over Na2SO4
  3. customthe solvent evaporated
  4. dissolutionThe residue was dissolved in 5 mL of THF
  5. additiontreated with 7.7 mL of a 1M BH3*THF-solution in THF
  6. temperaturerefluxed for 2 hrs
  7. customThe solvent was evaporated
  8. additionThe aqueous phase was then acidified by addition of an aqueous solution of HCl to a pH of ca. 7
  9. extractionextracted with Et2O
  10. dry with materialThe combined organic phases were dried over Na2SO4
  11. customthe solvent evaporated

Sources & evidence

ORD record
ord-91c8e6dbbf8f48a69f0e2aa6469b93fa
Source dataset
uspto-grants-2007_08
Patent number
US07259178B2

Reaction notes

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