Diisobutylaluminum hydride → (3,5-Diethoxypyridin-2-yl)methanol

HRID 1609829ノート

反応式

HRID 1609829 の反応式
C([O:3][C:4]([C:6]1[C:11]([O:12][CH2:13][CH3:14])=[CH:10][C:9]([O:15][CH2:16][CH3:17])=[CH:8][N:7]=1)=O)C.CC(C[AlH]CC(C)C)C>C(Cl)Cl.C1COCC1>[CH2:13]([O:12][C:11]1[C:6]([CH2:4][OH:3])=[N:7][CH:8]=[C:9]([O:15][CH2:16][CH3:17])[CH:10]=1)[CH3:14]

参加物

5

反応物 2

HCID 14487Diisobutylaluminum hydrideHCID 69650025HCID 69650025、化合物

生成物 1

HCID 22260398(3,5-Diethoxypyridin-2-yl)methanol収率 80.9%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To the 3,5-diethoxy-pyridine-2-carboxylic acid ethyl ester solution (250 mg, 1.04 mmol) in CH2Cl2 (10 ml), a solution of DIBAL in THF (1N, 3 mL) is added, and stirred at room temperature for 20 minutes. Excess reagent is quenched with Glauber's salt (Na2H2SO4·10H2O), filtered and concentrated to afford (3,5-diethoxy-pyridin-2-yl)-methanol (166 mg, 80% yield); 1H NMR (300 MHz, CDCl3): 7.77 (s, 1H), 6.69 (s, 1H), 4.65 (s, 2H), 4.15 (q, J=6.9 Hz, 2H), 3.65 (q, J=6.9 Hz, 2H), 1.45 (t, J=6.9 Hz, 6H).

後処理

  1. customExcess reagent is quenched with Glauber's salt (Na2H2SO4·10H2O)
  2. filtrationfiltered
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-eba854ff12154a10b7f305c9df0145c3
出典データセット
uspto-grants-2006_01
特許番号
US06982268B2

反応ノート

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