Sodium Thiosulfate → HCID 58443266, compound

HRID 1630743Notes

Reaction equation

HRID 1630743 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[C:12]([CH2:14][OH:15])[CH:11]=[CH:10][C:9]2=[O:16])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:9](=[O:16])[CH:10]=[CH:11][C:12]([CH:14]=[O:15])=[CH:13]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 584433001-(4-Fluorophenyl)-5-(hydroxymethyl)-2(1H)-pyridinone

Product 1

HCID 58443266HCID 58443266, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 100 mL round-bottomed flask was charged with 1-(4-fluorophenyl)-5-(hydroxymethyl)pyridin-2(1H)-one (0.420 g, 1.92 mmol) and 15 mL of CH2Cl2. To this was added Dess-Martin Periodinane (1.02 g, 2.39 mmol). After stirring at rt for 30 min, 15 mL of satd aq sodiumthiosulfate soln and 15 mL of satd aq sodium bicarbonate soln were added. The mixture was extracted with CH2Cl2 (3×30 mL) and the combined extracts were dried and concentrated. The residue was purified by MPLC to give 1-(4-fluorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarbaldehyde.

Workup

  1. extractionThe mixture was extracted with CH2Cl2 (3×30 mL)
  2. customthe combined extracts were dried
  3. concentrationconcentrated
  4. customThe residue was purified by MPLC

Sources & evidence

ORD record
ord-9f85519b96c841d085a4c6a2ca61e123
Source dataset
uspto-grants-2014_07
Patent number
US08791147B2

Reaction notes

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