Triacetoxyperiodinane → HCID 24754973, compound

HRID 268635Notes

Reaction equation

HRID 268635 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:9]([CH:10]([CH3:12])[CH3:11])=[C:8]([CH2:13][OH:14])[N:7]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[N:6]=1)=[O:4].C([O-])(O)=O.[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:9]([CH:10]([CH3:12])[CH3:11])=[C:8]([CH:13]=[O:14])[N:7]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[N:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 23665763Sodium BisulfiteHCID 247546741-(4-fluoro-phenyl)-5-hydroxymethyl-4-isopropyl-1H-pyrazole-3-carboxylic acid methyl ester

Product 1

HCID 24754973HCID 24754973, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-fluoro-phenyl)-5-hydroxymethyl-4-isopropyl-1H-pyrazole-3-carboxylic acid methyl ester (13.6 g, 46.7 mmol) in CH2Cl2 (300 mL) at 25° C. was added solid NaHCO3 (19.6 g, 233 mmol) followed by Dess Martin reagent (20.8 g, 49.0 mmol; commercially available from Lancaster). The reaction was stirred at 25° C. for 4 hr after which time saturated sodium bisulfite (50 mL) was added and the organic layer was separated and washed with water and brine. The organic layer was dried over Na2SO4and concentrated to an oil that was purified by silica gel chromatography (15% EtOAc/Hex) to afford 1-(4-fluoro-phenyl)-5-formyl-4-isopropyl-1H-pyrazole-3-carboxylic acid methyl ester (11.3 g, 84%): H-NMR (CDCl3) δ 9.95 (s, 1 H), 7.42-7.38 (m, 2 H), 7.17-7.13 (m, 2 H), 4.01-3.96 (m, 1 H), 3.92 (s, 3 H), 1.38 (d, 6 H).

Workup

  1. additionwas added
  2. customthe organic layer was separated
  3. washwashed with water and brine
  4. customThe organic layer was dried over Na2SO4and
  5. concentrationconcentrated to an oil that
  6. customwas purified by silica gel chromatography (15% EtOAc/Hex)

Sources & evidence

ORD record
ord-b8dd8b794ced4c53a2b2549f02b403fb
Source dataset
uspto-grants-2008_11
Patent number
US07446121B2

Reaction notes

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