Triacetoxyperiodinane → 4-Benzyloxy-2-formyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide

HRID 1177226Notes

Reaction equation

HRID 1177226 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([NH:7][C:8]([C:10]2[CH:20]=[C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:13]3[CH2:14][CH:15]([CH2:17][OH:18])[O:16][C:12]=3[CH:11]=2)=[O:9])=[N:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([NH:7][C:8]([C:10]2[CH:20]=[C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:13]3[CH2:14][CH:15]([CH:17]=[O:18])[O:16][C:12]=3[CH:11]=2)=[O:9])=[N:3]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 595600744-Benzyloxy-2-hydroxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide

Product 1

HCID 595602454-Benzyloxy-2-formyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amideYield 81.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-benzyloxy-2-hydroxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide (222a) (1.05 g, 2.77 mmol) in CH2Cl2 (25 mL) was added Dess-Martin periodinane (1.41 g, 3.32 mmol) at 0° C. The mixture was stirred at room temperature for 2 h. The reaction was quenched with saturated aqueous NaHCO3, extracted with 3×EtOAc, dried over Na2SO4, concentrated, and purified by flash column chromatography eluting with 55-100% EtOAc in hexanes to give a yellow foam (850 mg).

Workup

  1. customThe reaction was quenched with saturated aqueous NaHCO3
  2. extractionextracted with 3×EtOAc
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by flash column chromatography
  6. washeluting with 55-100% EtOAc in hexanes

Sources & evidence

ORD record
ord-c7d0f5c72f024e098b03bcc0deafdcf2
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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