Triacetoxyperiodinane → HCID 136338674, compound

HRID 2053415Notes

Reaction equation

HRID 2053415 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([C:13]1[O:17][N:16]=[C:15]([CH2:18][OH:19])[CH:14]=1)=[C:5]2[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>CC#N>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([C:13]1[O:17][N:16]=[C:15]([CH:18]=[O:19])[CH:14]=1)=[C:5]2[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 135545395HCID 135545395, compound

Product 1

HCID 136338674HCID 136338674, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 6-chloro-3-(3-hydroxymethyl-isoxazol-5-yl)-4-phenyl-1H-quinolin-2-one (822 mg, 2.33 mmol) in CH3CN (8 mL), Dess-Martin periodinane (1.05 g, 2.47 mmol) was added. The resulting mixture was stirred at RT for 3 hr and concentrated. Water (20 mL) was then added and the product was extracted with (5% MeOH: CH2Cl2 3×50 mL). The organic layer was dried (Na2SO4) and concentrated. The residue was chromatographed on silica (30-80% EtOAc:Hexane) to obtain partially pure 5-(6-chloro-2-oxo-4-phenyl-1,2-dihydro-quinolin-3-yl)-isoxazole-3-carboxaldehyde. Yield 66%: 1H-NMR (CDCl3; 400 MHz) δ 13.15 (s,1H), 10.09 (s, 1H), 7.57-7.47 (m, 8H), 6.97 (s,1H).

Workup

  1. concentrationconcentrated
  2. additionWater (20 mL) was then added
  3. extractionthe product was extracted with (5% MeOH: CH2Cl2 3×50 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica (30-80% EtOAc:Hexane)

Sources & evidence

ORD record
ord-6fb715a9730943bb908811f730990704
Source dataset
uspto-grants-2008_02
Patent number
US07326788B2

Reaction notes

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