Methanol → HCID 57597434, compound

HRID 887674Notes

Reaction equation

HRID 887674 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(OC(/N=N/C(OC(C)C)=O)=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CO>C1COCC1>[F:16][C:13]([F:14])([F:15])[C:8]([C:5]1[CH:4]=[CH:3][C:2]([NH2:1])=[CH:7][CH:6]=1)([O:17][CH3:18])[C:9]([F:10])([F:11])[F:12]

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 5778012-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-olHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 57597434HCID 57597434, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(4-amino-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol (1 eq.), DIAD (1.96 eq.), PPh3 (polymer-bound, 2.36 eq) and MeOH (1.1 eq) in THF (100 mL) was stirred at reflux for 16 h. After filtration and concentration, the crude was purified by flash chromatography (20% EtOAc/CH2Cl2) to give the title compound as a white solid. MS (ES+): 274 (M+H)+. Calc'd for C10H9F6NO—273.06.

Workup

  1. temperatureat reflux for 16 h
  2. filtrationAfter filtration and concentration
  3. customthe crude was purified by flash chromatography (20% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-df48a1d511eb4d92b71c5251d9522a2d
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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