Triacetoxyperiodinane → 3-(benzyloxy)cyclopentanone

HRID 237559Notes

Reaction equation

HRID 237559 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[CH2:1]([O:8][CH:9]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 577676553-(benzyloxy)cyclopentan-1-ol

Product 1

HCID 149370243-(benzyloxy)cyclopentanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 3-(benzyloxy)cyclopentanol (530 mg) in dichloromethane (8 mL) is added at 0° C. 1,1-dihydro-1,1,1-triacetoxy-1,2-benziodoxol-3(1H)-on (Dess-Martin periodinan, 8 mL of a 15% solution in dichloromethane). The mixture is stirred for 3 hours, diluted with dichloromethane, washed with 1 M aqueous NaOH solution and dried (MgSO4). The solvents are evaporated in vacuo and the residue is chromatographed on silica gel (petrole ether/ethyl acetate 90:10→40:60) to give the title compound. Yield: 430 mg; LC (method 7): tR=0.90 min; Mass spectrum (ESI+): m/z=191 [M+H]+.

Workup

  1. washwashed with 1 M aqueous NaOH solution
  2. dry with materialdried (MgSO4)
  3. customThe solvents are evaporated in vacuo
  4. customthe residue is chromatographed on silica gel (petrole ether/ethyl acetate 90:10→40:60)

Sources & evidence

ORD record
ord-d5fef09261df4488b11783c0e01ed5e8
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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