3-(3-Pyridyl)-2-propyn-1-ol → 3-(3-Pyridinyl)-2-propynal
反応式
[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]=1参加物
4
実験手順
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).
後処理
- additionThen the reaction mixture was poured on the top of a column of silica gel
- washeluted with cHex/EtOAc (2:1
出典と根拠
- ORDレコード
- ord-0d34f7fa59744093863db6505d5c49f8
- 出典データセット
- uspto-grants-2011_07
- 特許番号
- US07973039B2
反応ノート
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