Ethyl Acetate → 3-(2-Phenyl-6-trifluoromethylquinolin-3-yl)propan-1-ol

HRID 222553

Reaction equation

HRID 222553 reaction equation
[C:1]1([CH:7]2[CH:16]3[CH2:17][CH2:18][CH2:19][O:20][CH:15]3[C:14]3[CH:13]=[C:12]([C:21]([F:24])([F:23])[F:22])[CH:11]=[CH:10][C:9]=3[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+]([O-])([O-])=O.[NH4+].[Ce+4].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.C(OCC)(=O)C>C1COCC1>[C:1]1([C:7]2[C:16]([CH2:17][CH2:18][CH2:19][OH:20])=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:21]([F:24])([F:22])[F:23])[CH:13]=3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 9869224Ammonium cerium (IV) nitrateHCID 597804525-phenyl-9-trifluoromethyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline

Product 1

HCID 597804733-(2-Phenyl-6-trifluoromethylquinolin-3-yl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.50 g (1.50 mmol) of 5-phenyl-9-trifluoromethyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline 3 was dissolved in THF (15 ml), 1.65 g (3.00 mmol, 2 eq) of cerium(IV) ammonium nitrate were added at RT, and stirring was continued overnight at RT. When the reaction was complete, 50 ml of ethyl acetate were added, and the mixture was extracted 2× with 50 ml of water. The org. phase was dried and evaporated to dryness. The residue was recrystallised from ethyl acetate/diethyl ether, giving a pale-yellow solid (compound 4).

Workup

  1. extractionthe mixture was extracted 2× with 50 ml of water
  2. customphase was dried
  3. customevaporated to dryness
  4. customThe residue was recrystallised from ethyl acetate/diethyl ether

Sources & evidence

ORD record
ord-61e2bf49779b4b5b9d34b8f96db6338c
Source dataset
uspto-grants-2012_06
Patent number
US08207345B2

Linked notes

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