Diethyl Ether → HCID 178418743, compound

HRID 574696

Reaction equation

HRID 574696 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][OH:11])=[CH:9][C:4]=2[N:3]=[CH:2]1.C[N+]1([O-])CCOCC1.CCOCC>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[O:11])=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 82029Methyl morpholine oxideHCID 178519339HCID 178519339, compound

Product 1

HCID 178418743HCID 178418743, compound

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

(1H-benzo[d]imidazole-5-yl)methanol (2.8 mmol, 1 eq.) was dissolved in 30 mL dichloromethane and a molecular sieve (4 A) was added. To the solution were added Tetrapropylammonium perruthenate (0.28 mmol, 0.1 eq.) and N-Methylmorpholine-N-Oxide (9.8 mmol, 3.5 eq.). After stirring the mixture for 72 hours at room temperature 50 mL of ether was added and filtrated. The solvent was removed under reduced pressure and the product was purified by means of flash-chromatography using silica gel and a ethyl acetate/MeOH-gradient.

Workup

  1. additiona molecular sieve (4 A) was added
  2. additionwas added
  3. filtrationfiltrated
  4. customThe solvent was removed under reduced pressure
  5. customthe product was purified by means of flash-chromatography

Sources & evidence

ORD record
ord-12dc541905d04133a437a9cab93dbb56
Source dataset
uspto-grants-2015_05
Patent number
US09034907B2

Linked notes

Loading…