Triacetoxyperiodinane → 4-(3-Cyanophenyl)-cyclohexane-1-one

HRID 1393966Notes

Reaction equation

HRID 1393966 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C@H:9]2[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1)#[N:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 178509754HCID 178509754, compound

Product 1

HCID 114696954-(3-Cyanophenyl)-cyclohexane-1-oneYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The mixture of cis and trans 4-(3-cyanophenyl)-1-hydroxycyclohexane (1.8 g, 9 mmole) was dissolved in 100 ml methylene chloride and Dess-Martin reagent(4.2 g, 10 mmole) was added. The mixture was stirred at room temperature for five hours. The reaction solution was washed with water (3×100 mL) and dried over sodium sulfate. The product was purified by column chromatography using hexane/ethyl acetate (85/15) as the eluent to afford 4-(3-cyanophenyl)-cyclohexane-1-one (1,1 g, 63%).

Workup

  1. washThe reaction solution was washed with water (3×100 mL)
  2. dry with materialdried over sodium sulfate
  3. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-7b5066a067c242a18c633d50f431a524
Source dataset
uspto-grants-2008_03
Patent number
US07348328B2

Reaction notes

Loading…