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Trifluoroacetic acid → 4-Oxo-3-(quinolin-3-yl)-butyric acid ethyl ester

HRID 1004286
Notes
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Reaction equation

HRID 1004286 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH:6]([C:10]1[CH:11]=[N:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=CC)[CH3:2].C(O)(C(F)(F)F)=[O:22].O=[O+][O-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH:6]([C:10]1[CH:11]=[N:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=[O:22])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11776TriphenylphosphineHCID 24823OzoneHCID 541558463-(Quinolin-3-yl)-hex-4-enoic acid ethyl ester

Product 1

HCID 537991904-Oxo-3-(quinolin-3-yl)-butyric acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

A solution of 22-3 (1.0 g, 3.7 mmol), TFA (0.06 mL, 3.9 mmol), and sudan red (0.5 mg) in anhydrous CH2Cl2 (50 mL) was cooled to -78° and treated with O3 until the sudan red color disappeared (5 min). Solid Ph3P (1.4 g, 5.6 mmol) was added and the solution warmed to room temperature. After 30 min., the solution was washed with sat. NaHCO3, dried, filtered, and evaporated. Chromatography on silica gel (10% acetone/EtOAc) afforded 22-4 as colorless glass.

Workup

  1. custom(5 min)
  2. washthe solution was washed with sat. NaHCO3
  3. customdried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-175220301ebc4b0bbf259969f6696056
Source dataset
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06048861

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes