Triacetoxyperiodinane → 5-Fluoro-2-methoxy-4-(2-oxoethyl)benzonitrile

HRID 1186986Notes

Reaction equation

HRID 1186986 reaction equation
[F:1][C:2]1[C:3]([CH2:12][CH2:13][OH:14])=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[C:7]#[N:8].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>[F:1][C:2]1[C:3]([CH2:12][CH:13]=[O:14])=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

6

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 666439605-Fluoro-4-(2-hydroxyethyl)-2-methoxybenzonitrile

Product 1

HCID 866944585-Fluoro-2-methoxy-4-(2-oxoethyl)benzonitrile

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 24477Sodium ThiosulfateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 5-fluoro-4-(2-hydroxyethyl)-2-methoxybenzonitrile (175 mg, 0.900 mmol) in Dichloromethane (4 mL) was added Dess-Martin Periodinane (0.53 g, 1.2 mmol). The solution was stirred for 2 h at ambient temperature, then was diluted with NaHCO3 (sat.) and Na2S2O3 (sat.) and stirred for 30 min. The layers were separated and the aqueous layer was extracted with dichloromethane twice. The combined organics were washed with brine, dried (MgSO4), filtered, and concentrated to provide the desired aldehyde, which was used directly without further purification.

Workup

  1. stirringstirred for 30 min
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with dichloromethane twice
  4. washThe combined organics were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-01bf440fec8b4a0ba2c12e051da10505
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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