Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 10154224, compound

HRID 279175Notes

Reaction equation

HRID 279175 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:18])[C@@H:9]([O:11]C1CCCCO1)[CH3:10].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:18])[C@@H:9]([OH:11])[CH3:10]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 10264208HCID 10264208, compound

Product 1

HCID 10154224HCID 10154224, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

(2S)-2′-Fluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propiophenone (25 g) was dissolved in ethanol (200 ml), to which pyridinium p-toluenesulfonate (1.28 g) was added. The reaction solution was stirred at 55° C. for 2.5 hours and then concentrated. The residue was subjected to silica gel chromatography (eluent: hexane/ethyl acetate=9/1 to 5/1) to give (2S)-2′-fluoro-2-hydroxypropiophenone (16.4 g) as a colorless oily substance.

Workup

  1. additionwas added
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-66ae20787e1842d8aec3a220eeedb9d0
Source dataset
uspto-grants-2002_03
Patent number
US06362206B1

Reaction notes

Loading…