HCID 12181442, compound → 3-(3-Pyridinyl)-2-propynal

HRID 1008761Notes

Reaction equation

HRID 1008761 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]#[C:8][CH2:9][OH:10])[CH:2]=1>C(Cl)Cl.O=[Mn]=O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]#[C:8][CH:9]=[O:10])[CH:2]=1

Participants

4

Reactant 1

HCID 12181442HCID 12181442, compound

Product 1

HCID 227351693-(3-Pyridinyl)-2-propynalYield 17.4%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(3-pyridinyl)-2-propyn-1-ol (250 mg, 1.88 mmol, obtained as described in J. Org Chem. 1998, 63, 1109-1118) in anhydrous DCM (10 ml) under argon was added MnO2 (3.66 g, 42 mmol) portion wise over 1.5 h. The reaction mixture was stirred at rt for one additional hour. Then the reaction mixture was poured on the top of a column of silica gel and eluted with cHex/EtOAc (2:1 then 1:1) to give 43 mg (17%) of the title compound as a yellow powder. 1H NMR (CDCl3) δ: 9.46 (s, 1H), 8.85 (dd, J=2.1, 0.8 Hz, 1H), 8.71 (dd, J=5.0, 1.7 Hz, 1H), 7.91 (ddd, J=8.0, 2.1, 1.7 Hz, 1H), 7.38 (ddd, J=8.0, 5.0, 0.8 Hz, 1H).

Workup

  1. additionThen the reaction mixture was poured on the top of a column of silica gel
  2. washeluted with cHex/EtOAc (2:1

Sources & evidence

ORD record
ord-0d34f7fa59744093863db6505d5c49f8
Source dataset
uspto-grants-2011_07
Patent number
US07973039B2

Reaction notes

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