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

HRID 379266Notes

Reaction equation

HRID 379266 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]

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 6344DichloromethaneSolvent

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-82ce3421100f4c2094899fc9bc20e815
Source dataset
uspto-grants-2001_10
Patent number
US06297249B1

Reaction notes

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