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

HRID 1053980Notes

Reaction equation

HRID 1053980 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-525beb2dd93f460b8c2c092e885a37eb
Source dataset
uspto-grants-2016_07
Patent number
US09394284B2

Reaction notes

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