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

HRID 1519541Notes

Reaction equation

HRID 1519541 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+].S([O-])([O-])(=O)=S.[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, 0.90 mmol) in dichloromethane (4 mL) was added Dess-Martin periodinane (530 mg, 1.3 mmol) at RT. The mixture stirred at roomtemperature for 2 h, then was diluted with saturated sodium bicarbonate and saturated sodium thiosulfate and stirred 30 min. The mixture was extracted with dichloromethane (3×) and the combined organics dried (MgSO4), filtered and concentrated to provide 5-fluoro-2-methoxy-4-(2-oxoethyl)benzonitrile which was used without further purification. LC-MS (IE, m/z): 194.2 [M+1]+.

Workup

  1. stirringstirred 30 min
  2. extractionThe mixture was extracted with dichloromethane (3×)
  3. dry with materialthe combined organics dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-38da3e0c857e4655b0fe50905e756054
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

Loading…