5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid → 3-Benzyloxy-4-pyrone

HRID 571053Notes

Reaction equation

HRID 571053 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:18])[CH:11]=[C:12](C(O)=O)[O:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>N1C2C(=CC=CC=2)C=CC=1>[CH2:1]([O:8][C:9]1[C:10](=[O:18])[CH:11]=[CH:12][O:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 64807825-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid

Product 1

HCID 108996783-Benzyloxy-4-pyrone

Reagents, catalysts & solvents 1

HCID 7047QuinolineSolvent

Procedure

5-(Benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid (68.9 g, 280 mmol) was added to 300 mL of quinoline at 235° C. and the mixture was heated at reflux for 30 min. The mixture was cooled to room temperature and concentrated to give a residue which was purified by silica gel chromatography to give 3-(benzyloxy)-4H-pyran-4-one, 1H-NMR (CDCl3, 400 MHz) δ 7.64 (dd, J=5.6, 0.8 Hz, 1H), 7.53 (d, J=0.4 Hz, 1H), 7.39-7.28 (m, 5H), 6.40(d, J=5.6 Hz, 1H), 5.06 (s, 2H). MS (M+H)+ 203.0.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 30 min
  3. concentrationconcentrated
  4. customto give a residue which
  5. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-3edd54aae96145aa94d61c73d2fb0472
Source dataset
uspto-grants-2015_05
Patent number
US09024032B2

Reaction notes

Loading…