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

HRID 992932

Reaction equation

HRID 992932 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-8efc56012e054d159c62b8cc0a7c2edd
Source dataset
uspto-grants-2002_10
Patent number
US06472372B1

Linked notes

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