Triacetoxyperiodinane → HCID 22350127, compound

HRID 896674Notes

Reaction equation

HRID 896674 reaction equation
[CH3:1][S:2]([C:5]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:19]=[C:20]([CH2:24][CH:25]([C:34]4[CH:39]=[CH:38][C:37]([S:40][CH3:41])=[CH:36][CH:35]=4)[CH:26]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[OH:27])[CH:21]=[CH:22][CH:23]=3)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([CH3:7])[CH3:6])(=[O:4])=[O:3].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>[CH3:1][S:2]([C:5]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:19]=[C:20]([CH2:24][CH:25]([C:34]4[CH:35]=[CH:36][C:37]([S:40][CH3:41])=[CH:38][CH:39]=4)[C:26]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)=[O:27])[CH:21]=[CH:22][CH:23]=3)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([CH3:7])[CH3:6])(=[O:3])=[O:4]

Participants

6

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 22350120HCID 22350120, compound

Product 1

HCID 22350127HCID 22350127, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
21 °C

Procedure

To a solution of the crude oil from Step 3 in CH2Cl2 (5 mL) at 21° C. was added Dess-Martin periodinane (255 mg, 0.6 mmol) portionwise. The resulting reaction mixture was stirred 2 h at 21° C., then diluted with a sodium bicarbonate solution and ethyl acetate. The organic extracts were washed (H2O), (brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (eluting with hexane/ethyl acetate, 50:50) provided the 3-{3-[6-(1-methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-phenyl}-2-(4-methylsulfanyl-phenyl)-1-phenyl-propan-1-one compound as a white foam.

Workup

  1. customThe resulting reaction mixture
  2. washThe organic extracts were washed (H2O), (brine),
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification
  7. washby flash chromatography (eluting with hexane/ethyl acetate, 50:50)

Sources & evidence

ORD record
ord-0029a14c78cf436eb00ef4ce077ecc28
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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