Triacetoxyperiodinane → Methyl 6-formylpyridine-3-carboxylate

HRID 341519

Reaction equation

HRID 341519 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH2:24][C:25]1[N:30]=[CH:29][C:28]([C:31]([O:33][CH3:34])=[O:32])=[CH:27][CH:26]=1>C(Cl)Cl>[CH:24]([C:25]1[N:30]=[CH:29][C:28]([C:31]([O:33][CH3:34])=[O:32])=[CH:27][CH:26]=1)=[O:23]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 7894146-Hydroxymethyl-nicotinic acid methyl ester2×

Product 1

HCID 586269Methyl 6-formylpyridine-3-carboxylateYield 105%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dess-Martin periodinane (2.54 g, 5.98 mmol) was added to a solution of methyl 6-(hydroxymethyl)pyridine-3-carboxylate (Intermediate 190, 1.00 g, 5.98 mmol) in DCM (75 mL) at room temperature. The reaction mixture was stirred at room temperature for 24 hrs before being diluted with DCM (50 mL), washed with a 1:1 mixture of saturated aqueous solution of sodium bicarbonate and sodium thiosulfate (3×75 mL). The organic phase was dried over sodium sulfate, filtered and evaporated under vacuum to provide the title compound (1.02 g, 105%). Method B HPLC-MS: MH+ requires m/z=166 Found: m/z=166, Rt=1.44 min (62%).

Workup

  1. washwashed with a 1:1 mixture of saturated aqueous solution of sodium bicarbonate and sodium thiosulfate (3×75 mL)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-b231342f377b4faeb25c62d2e8ca62f1
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Linked notes

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