Triacetoxyperiodinane → 2-Bromo-4-methoxycyclopentanone

HRID 541467Notes

Reaction equation

HRID 541467 reaction equation
[Br:1][CH:2]1[CH2:6][CH:5]([O:7][CH3:8])[CH2:4][CH:3]1[OH:9].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl.O>[Br:1][CH:2]1[CH2:6][CH:5]([O:7][CH3:8])[CH2:4][C:3]1=[O:9]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 682882462-Bromo-4-methoxycyclopentanol2×

Product 1

HCID 682881302-Bromo-4-methoxycyclopentanoneYield 134.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Into a round-bottom flask, was placed a solution of 2-Bromo-4-methoxycyclopentanol (compound 461.3, 1.00 g, 3.08 mmol, 1.00 equiv, 60%) in dichloromethane (100 mL). Dess-Martin periodinane (2.00 g, 4.72 mmol, 1.10 equiv) was added in portions and the mixture was stirred overnight at room temperature. The mixture was then diluted with water (20 mL) and quenched with Na2S2O4 (4 g). The aqueous was extracted with dichloromethane (100 mL) and the combined organics was washed with brine (30 mL), dried (Na2SO4), filtered and concentrated in vacuo to obtain the title compound as a brown oil (800 mg, 81%).

Workup

  1. customInto a round-bottom flask, was placed
  2. customquenched with Na2S2O4 (4 g)
  3. extractionThe aqueous was extracted with dichloromethane (100 mL)
  4. washthe combined organics was washed with brine (30 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-33acbc1fd02545ffafd1a9e24113ad0f
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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