Triacetoxyperiodinane → HCID 13445263, compound

HRID 1948535Notes

Reaction equation

HRID 1948535 reaction equation
[OH:1][CH:2]([C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1)[CH:3]([CH3:5])[CH3:4].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:2]([C:6]1[CH:7]=[CH:8][C:9]([C:10]#[N:11])=[CH:12][CH:13]=1)(=[O:1])[CH:3]([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 11480758HCID 11480758, compound

Product 1

HCID 13445263HCID 13445263, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 4-(1-hydroxy-2-methylpropyl)benzonitrile (2.500 g, 14.27 mmol) (Prepared according to the method of Keh et al., J. Amer. Chem. Soc., 125(14):4062-4063 (2003)) in dry DCM (200 mL) was added Dess-Martin Periodinane (7.26 g, 17.12 mmol The reaction mixture was stirred for 2 h. The reaction mixture was diluted with DCM and washed with 1N NaOH solution. The organic layer was dried with MgSO4, filtered, and concentrated to yield 2.4 g of 4-isobutyrylbenzonitrile. MS (m+1)=174. HPLC Peak RT=1.60 minutes (Analytical Method B).

Workup

  1. washwashed with 1N NaOH solution
  2. dry with materialThe organic layer was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6a0484a5b26447ab96dec8a754c358e9
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

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