Triacetoxyperiodinane → 5-Chloro-4-formylthiophene-2-carbonitrile

HRID 34073Notes

Reaction equation

HRID 34073 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]#[N:8])=[CH:4][C:3]=1[CH2:9][OH:10].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[Cl:1][C:2]1[S:6][C:5]([C:7]#[N:8])=[CH:4][C:3]=1[CH:9]=[O:10]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 230701655-Chloro-4-hydroxymethylthiophene-2-carbonitrile

Product 1

HCID 230702115-Chloro-4-formylthiophene-2-carbonitrileYield 151.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3.0 g of 5-chloro-4-hydroxymethylthiophene-2-carbonitrile in 34 mL of dichloromethane was added 8.06 g of Dess-Martin reagent at room temperature, and stirred at this temperature for a day. After diluting with dichloromethane, washing successively with aqueous sodium hydrogen carbonate and saturated brine, and drying over anhydrous magnesium sulfate, the solvent was evaporated, to afford 4.5 g of a crude product of the title compound as colorless crystals.

Workup

  1. washwashing successively with aqueous sodium hydrogen carbonate and saturated brine
  2. dry with materialdrying over anhydrous magnesium sulfate
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-fc6f0aba60704c4dabaaa80653a14acb
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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