Triacetoxyperiodinane → 3-(3-Quinolinyl)-2-propynal

HRID 2416452Notes

Reaction equation

HRID 2416452 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]#[C:12][CH2:13][OH:14])[CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]#[C:12][CH:13]=[O:14])[CH:2]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 6501423-Quinolin-3-ylprop-2-yn-1-ol

Product 1

HCID 226307723-(3-Quinolinyl)-2-propynalYield 72.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(3-quinolinyl)-2-propyn-1-ol (prepared as described in J. Med Chem. 1996, 39, 3179) (360 mg, 1.96 mmol) and the Dess-Martin reagent (1.00 g, 2.36 mmol) in dichloromethane (10 mL) was stirred at RT for 1.5 h. The solution was washed with sat. aq. NaHCO3 and brine, dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 1:4 hexane/ethyl acetate) yielded 258 mg (72%) of the title compound. MS 182 (M+H)+.

Workup

  1. washThe solution was washed with sat. aq. NaHCO3 and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customPurification by chromatography (SiO2, 1:4 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-61daffd21625433a8f545c22df1e8532
Source dataset
uspto-grants-2004_11
Patent number
US06825170B2

Reaction notes

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