Triacetoxyperiodinane → 4-(2-Oxoethyl)-1-naphthonitrile

HRID 1519546Notes

Reaction equation

HRID 1519546 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]#[N:15])=[CH:6][CH:5]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[O:1]=[CH:2][CH2:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]#[N:15])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 139983804-(2-Hydroxyethyl)-1-naphthonitrile

Product 1

HCID 874283114-(2-Oxoethyl)-1-naphthonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(2-hydroxyethyl)naphthalene-1-carbonitrile (25 mg, 0.13 mmol) in DCM (4 mL) was treated with Dess-Martin periodinane (75 mg, 0.18 mmol) and was stirred at room temperature for 3 hours. The reaction was quenched by partitioning with DCM and water containing sodium bicarbonate and sodium thiosulfate (3×). The organic layer was then washed with brine, dried over sodium sulfate and evaporated to give the title aldehyde as an oil which was used directly in subsequent reductive amination reaction.

Workup

  1. customThe reaction was quenched
  2. customby partitioning with DCM and water
  3. additioncontaining sodium bicarbonate and sodium thiosulfate (3×)
  4. washThe organic layer was then washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-d05870cf76044e24b81179329882007b
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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