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

HRID 1837923Notes

Reaction equation

HRID 1837923 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-19c324de00c44ecfb36f37b924407a7e
Source dataset
uspto-grants-2004_08
Patent number
US06784190B2

Reaction notes

Loading…