Triacetoxyperiodinane → HCID 58075506, compound

HRID 451092Notes

Reaction equation

HRID 451092 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:10]2[CH2:14][CH2:13][CH2:12][C@@H:11]2[OH:15])[CH:5]=[C:6]([F:9])[C:7]=1[F:8].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:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:5]=[C:6]([F:9])[C:7]=1[F:8]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58075730HCID 58075730, compound

Product 1

HCID 58075506HCID 58075506, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (1S,2R)-2-(3,4,5-trifluorophenyl)cyclopentanol (1 g, 4.63 mmol) in CH2Cl2 (20 mL) was added Dess-Martin periodinane (2.354 g, 5.55 mmol). The reaction mixture was stirred at rt for 1 h. The reaction 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-(3,4,5-trifluorophenyl)cyclopentanone (310 mg, 1.447 mmol, 31.3% yield). LC-MS (M+H)+=215.1.

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-9c26c4aa596f4a5da10da94a0a4a5b70
Source dataset
uspto-grants-2013_07
Patent number
US08486952B2

Reaction notes

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