Triacetoxyperiodinane → 2-(4-Fluorophenyl)cyclohexan-1-one

HRID 347298Notes

Reaction equation

HRID 347298 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]2[OH:14])=[CH:4][CH:3]=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]=[CH:4][C:5]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=[O:14])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 20487437HCID 20487437, compound

Product 1

HCID 130895402-(4-Fluorophenyl)cyclohexan-1-oneYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

bi) To a solution of rac-2-(4-fluoro-phenyl)-cyclohexanol (3.8 g, 20 mmol) in DCM (320 mL) was added Dess-Martin periodinane [1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one](10 g, 24 mmol) at room temperature and after 2 h the reaction mixture was washed with sodium hydrogen carbonate (10%, 150 mL). The organic phase was then separated and washed with sodium thiosulfite (10%, 150 mL) and then dried over sodium sulfate, filtered and evaporated. Purification by chromatography through silica gel, eluting with ethyl acetate:hexane (1:4) afforded the title compound (3.4 g, 89%) as white crystals. MS: m/e=192.1 (M).

Workup

  1. washafter 2 h the reaction mixture was washed with sodium hydrogen carbonate (10%, 150 mL)
  2. customThe organic phase was then separated
  3. washwashed with sodium thiosulfite (10%, 150 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by chromatography through silica gel
  8. washeluting with ethyl acetate:hexane (1:4)

Sources & evidence

ORD record
ord-35ea9da48c314b56b53ad39c68e8ee26
Source dataset
uspto-grants-2007_02
Patent number
US07173133B2

Reaction notes

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