Acetic Anhydride → HCID 2323445, compound

HRID 854476Notes

Reaction equation

HRID 854476 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:20]>N1C=CC=CC=1>[F:16][C:13]([F:14])([F:15])[C:8]([C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:19](=[O:20])[CH3:18])=[CH:7][CH:6]=1)([OH:17])[C:9]([F:10])([F:11])[F:12]

Participants

4

Reactant 2

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

Product 1

HCID 2323445HCID 2323445, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 5 g (19.3 mmol) of 2-(4-amino-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol in 25 mL of pyridine was treated with 2.2 mL (23.3 mmol) of Ac2O. The mixture was stirred at 60° C. for 2 hours and the solvent partially evaporated. The residue was distributed between a diluted aqueous solution of HCl and Et2O. The combined organic phases were dried over Na2SO4 and evaporated to yield 5.7 g of crude N-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenyl]-acetamide that was dissolved in 100 mL of DMF, treated with 3.4 mL (22.7 mmol) of DBU and then dropwise at 0° C. with 3.8 mL (22.7 mmol) of TESCI. The mixture was stirred at RT for 10 hours and then poured into a saturated aqueous solution of NH4Cl and Et2O. The phases were separated and the aqueous one was extracted with Et2O. The combined organic phases were dried over Na2SO4 and evaporated to yield 8.3 g of crude N-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-phenyl]-acetamide which was dissolved in 100 mL of THF and treated with 3.4 mL of a 1M BH3*THF-solution in THF. The mixture was kept at reflux for 4 hours and the solvent partially evaporated. After addition of a saturated aqueous solution of NH4Cl and Et2O, the phases were separated and the aqueous one was extracted with Et2O. The combined organic phases were dried over Na2SO4 and evaporated. Column chromatography on silica gel with n-heptane/EtOAc 9:1 yielded 7.5 g (96%) of ethyl-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-phenyl]-amine, light yellow oil, MS: 402 (MH+).

Workup

  1. customthe solvent partially evaporated
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-dd759b05683e4a98a9024228aa2bdc5a
Source dataset
uspto-grants-2007_08
Patent number
US07259178B2

Reaction notes

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