Triacetoxyperiodinane → HCID 86635916, compound

HRID 561806Notes

Reaction equation

HRID 561806 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:15]=[C:14]([CH2:16][OH:17])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:15]=[C:14]([CH:16]=[O:17])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 66760794HCID 66760794, compound

Product 1

HCID 86635916HCID 86635916, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [2-(3-methoxypropyl)quinoline-4-yl]methanol from the previous step (1 eq.) in CH2Cl2 (0.05 M) was added Dess-Martin periodinane (1.1 eq.) portionwise. The resulting suspension was stirred at RT for 3 h. The reaction was quenched with MeOH and H2O. The organic layer was separated and the aqueous layer was back-extracted with EtOAc. The combined organic extracts were washed sat. aq. NaHCO3 and brine, dried over Na2SO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound which was purified further by way of flash chromatography (SiO2, 2:1 (v/v) Hex:EtOAc).

Workup

  1. customThe reaction was quenched with MeOH and H2O
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was back-extracted with EtOAc
  4. washThe combined organic extracts were washed sat. aq. NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-ab46bd22e79344638e0d84332986ed17
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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