Triacetoxyperiodinane → HCID 86713810, compound

HRID 521861Notes

Reaction equation

HRID 521861 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]2[CH2:13][O:12][CH2:11][CH:10]([OH:14])[CH2:9][CH2:8]2)=[C:5]([N+:15]([O-:17])=[O:16])[CH:4]=[N:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][N:2]1[C:6]([CH:7]2[CH2:13][O:12][CH2:11][C:10](=[O:14])[CH2:9][CH2:8]2)=[C:5]([N+:15]([O-:17])=[O:16])[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 86713809HCID 86713809, compound

Product 1

HCID 86713810HCID 86713810, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(2-methyl-4-nitro-pyrazol-3-yl)oxepan-3-ol (53 mg, 0.22 mmol) in DCM (6 mL) was added Dess-Martin periodinane (192 mg, 0.44 mmol) and sodium bicarbonate (93 mg, 1.10 mmol). The mixture was stirred at room temperature overnight, quenched with water, and extracted with DCM (3×). Combined organic layers were concentrated to dryness and purified via silica gel chromatography (0-100% EtOAc/heptane) to afford 6-(2-methyl-4-nitro-pyrazol-3-yl)oxepan-3-one (53 mg, quant.).

Workup

  1. customquenched with water
  2. extractionextracted with DCM (3×)
  3. concentrationCombined organic layers were concentrated to dryness
  4. custompurified via silica gel chromatography (0-100% EtOAc/heptane)

Sources & evidence

ORD record
ord-7dcbbf3ea0a04ba5be310904c478846a
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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