Triacetoxyperiodinane → 1-[5-Chloro-2-(4-chloro-benzyloxy)-benzyl]-5-methyl-1H-pyrazole-3-carbaldehyde

HRID 536560Notes

Reaction equation

HRID 536560 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[C:6]([CH:16]=1)[CH2:7][N:8]1[C:12]([CH3:13])=[CH:11][C:10]([CH2:14][OH:15])=[N:9]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=2)=[C:6]([CH:16]=1)[CH2:7][N:8]1[C:12]([CH3:13])=[CH:11][C:10]([CH:14]=[O:15])=[N:9]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 68641874{1-[5-Chloro-2-(4-chloro-benzyloxy)-benzyl]-5-methyl-1H-pyrazol-3-YL}-methanol

Product 1

HCID 866856891-[5-Chloro-2-(4-chloro-benzyloxy)-benzyl]-5-methyl-1H-pyrazole-3-carbaldehydeYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of alcohol 4 (0.57 g, 1.3 mmol) and 0.5 M Dess-Martin periodinane (9.05 mL, 4.1 mmol) in CH2Cl2 (25 mL) was stirred under N2 atmosphere at RT for 3 h. The reaction mixture was quenched with a 10% aqueous solution of Na2S2O3 (10 mL) and extracted with more CH2Cl2 (10 mL). The organic layer was washed with water (10 mL), dried (Na2SO4) and the volatiles were removed in vacuo. The residue was purified by MPLC (5 g SiO2 cartridge, eluent 70% iso-hexane-30% CH2Cl2) to give aldehyde 5 0.3 g (64%).

Workup

  1. customThe reaction mixture was quenched with a 10% aqueous solution of Na2S2O3 (10 mL)
  2. extractionextracted with more CH2Cl2 (10 mL)
  3. washThe organic layer was washed with water (10 mL)
  4. dry with materialdried (Na2SO4)
  5. customthe volatiles were removed in vacuo
  6. customThe residue was purified by MPLC (5 g SiO2 cartridge, eluent 70% iso-hexane-30% CH2Cl2)

Sources & evidence

ORD record
ord-a031953bf19c4964bde9a886c2ec768b
Source dataset
uspto-grants-2014_10
Patent number
US08859606B2

Reaction notes

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