Triacetoxyperiodinane → HCID 178519862, compound

HRID 1424689Notes

Reaction equation

HRID 1424689 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 it 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-1ff55ee479814ae4b41cb9b419ec7337
Source dataset
uspto-grants-2015_01
Patent number
US08927738B2

Reaction notes

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