Triacetoxyperiodinane → 2-(3,5-Difluorophenyl)cyclopentanone

HRID 2370168Notes

Reaction equation

HRID 2370168 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[CH2:13][CH2:12][CH2:11][C@@H:10]2[OH:14])[CH:5]=[C:6]([F:8])[CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:13][CH2:12][CH2:11][C:10]2=[O:14])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 10976443(1S,2R)-2-(3,5-difluorophenyl)cyclopentanol

Product 1

HCID 580758212-(3,5-Difluorophenyl)cyclopentanoneYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (1S,2R)-2-(3,5-difluorophenyl)cyclopentanol (6 g, 30.3 mmol) in CH2Cl2 (150 mL) was added Dess-Martin periodinane (15.41 g, 36.3 mmol). The reaction mixture was stirred at rt for 3 h. The reaction mixture was diluted with dichloromethane and quenched with the addition of 1 N NaOH. The organic layer was collected, dried (Na2SO4) and concentrated. The crude product was purified by column chromatography on silica gel to afford 2-(3,5-difluorophenyl)cyclopentanone (4.765 g, 24.29 mmol, 80% yield). LC-MS (M+H)+=197.0. 1H NMR (500 MHz, CDCl3) δ ppm 6.70 (2H, d, J=6.7 Hz), 6.52-6.67 (1H, m), 3.17-3.33 (1H, m), 2.33-2.56 (2H, m), 2.06-2.26 (2H, m), 2.01 (1H, dd, J=11.7, 6.3 Hz), 1.89 (1H, br s).

Workup

  1. customquenched with the addition of 1 N NaOH
  2. customThe organic layer was collected
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-bdef4555c25e4534bf4ba31954e3302f
Source dataset
uspto-grants-2014_04
Patent number
US08710061B2

Reaction notes

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