Triacetoxyperiodinane → HCID 178519862, compound

HRID 1888335Notes

Reaction equation

HRID 1888335 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[C:28]1[NH:29][CH:30]=[C:31]([CH2:33][OH:34])[N:32]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[C:28]1[NH:29][CH:30]=[C:31]([CH:33]=[O:34])[N:32]=1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 178519863HCID 178519863, compound

Product 1

HCID 178519862HCID 178519862, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dess-Martin periodinane (4.71 g, 11.1 mmol) was added to a stirred suspension of (2-Thiophen-2-yl-1H-imidazol-4-yl)-methanol (2.00 g, 11.1 mmol) dissolved in Methylene chloride (111 mL) at rt under Ar. The mixture turned dark and was stirred at rt ON. More DCM (100 ml) and sat NaHCO3 (100 mL) were added and the phases were separated after filtration to remove some solid. The organic layer was loaded onto silica gel and was purified by silica gel chromatography (Eluent: 0-100% EtOAc in n-heptane). Yield 0.57 g of the title compound as a red solid. LC-MS: m/z=178.6 (MH+), tR=0.31 min, method C.

Workup

  1. additionwere added
  2. customthe phases were separated
  3. filtrationafter filtration
  4. customto remove some solid
  5. customwas purified by silica gel chromatography (Eluent: 0-100% EtOAc in n-heptane)

Sources & evidence

ORD record
ord-ca0fa807b71048d2b8ab39c20cbb23bf
Source dataset
uspto-grants-2013_08
Patent number
US08501797B2

Reaction notes

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