Triacetoxyperiodinane → 1-(Isoquinolin-5-yl)ethan-1-one

HRID 446768Notes

Reaction equation

HRID 446768 reaction equation
[CH:1]1[C:10]2[C:5](=[C:6]([CH:11]([OH:13])[CH3:12])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:1]1[C:10]2[C:5](=[C:6]([C:11](=[O:13])[CH3:12])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 204934341-(Isoquinolin-5-yl)ethanol

Product 1

HCID 204934691-(Isoquinolin-5-yl)ethan-1-oneYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 10° C. solution of 1-(isoquinolin-5-yl)ethanol (530 mg, 3.0 mmol) in DCM (10 mL) was added Dess-Martin periodinane (1.9 g, 4.0 mmol) under a N2 atmosphere. The reaction mixture was stirred for 16 h at room temperature and then quenched with saturated NaHCO3 solution (5 mL). The organic layer was separated, washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography using 20% ethyl acetate in hexanes to afford 1-(isoquinolin-5-yl)ethanone (500 mg, 95.4%) as an off-white solid.

Workup

  1. customquenched with saturated NaHCO3 solution (5 mL)
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto obtain the crude product
  8. customThe crude material was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-6dc9914098e9447f951997781c3eb2a1
Source dataset
uspto-grants-2013_07
Patent number
US08481532B2

Reaction notes

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