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

HRID 1489423Notes

Reaction equation

HRID 1489423 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 200 ml of ethanol, to which 1.28 g of pyridinium p-toluenesulfonate was added. The mixture was stirred at 55° C. for 2.5 hours and then concentrated. The residue was purified by silica gel chromatography (eluent; hexane:ethyl acetate=9:1 to 5:1) to give 16.4 g of (2S)-2'-fluoro-2-hydroxypropiophenone as a colorless oil.

Workup

  1. additionwas added
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel chromatography (eluent; hexane:ethyl acetate=9:1 to 5:1)

Sources & evidence

ORD record
ord-c5de8fa4a2b040bd85783e6e46f21f0d
Source dataset
uspto-grants-1997_10
Patent number
US05677464

Reaction notes

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