5-Butyl-pyridine-2-carboxylic acid methoxy-methyl-amide → 1-(5-Butyl-pyridin-2-yl)-ethanone

HRID 724475

反応式

HRID 724475 の反応式
[CH3:1][Mg+].[Br-].CON(C)[C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH3:18])=[CH:11][N:10]=1)=[O:8]>C1COCC1>[CH2:15]([C:12]1[CH:13]=[CH:14][C:9]([C:7](=[O:8])[CH3:1])=[N:10][CH:11]=1)[CH2:16][CH2:17][CH3:18]

参加物

4

反応物 2

HCID 587470075-Butyl-pyridine-2-carboxylic acid methoxy-methyl-amideHCID 178418689HCID 178418689、化合物

生成物 1

HCID 124362861-(5-Butyl-pyridin-2-yl)-ethanone収率 96.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

MeMgBr (1.98 ml, 5.94 mmol) was added to a solution of 5-butyl-pyridine-2-carboxylic acid methoxy-methyl-amide (I-2A-38a; 880 mg, 3.96 mmol) in THF (10 ml) at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred for 1.5 h, quenched with saturated aqueous NH4Cl (1 ml), and saturated aqueous NaCl. The aqueous THF solution was extracted with EtOAc (2×), and the combined organic extracts were washed with saturated aqueous NaCl, dried, and concentrated under vacuum to yield the product I-2A-38b as an oil (680 mg): APcl MS 178.1 (M+1)+; 1H NMR (400 MHz, CDCl3) δ 8.47 (d, 1H, J=1.6 Hz), 7.95 (d, 1H, J=8.3 Hz), 7.60 (dd, 1H, J=1.6, 8.3 Hz), 2.69 (s, 3H), 2.67 (t, 2H, J=7.9 Hz), 1.65–1.56 (m, 2H), 1.40–1.30 (m, 2H), 0.92 (t, 3H, J=7.4 Hz).

後処理

  1. customquenched with saturated aqueous NH4Cl (1 ml), and saturated aqueous NaCl
  2. extractionThe aqueous THF solution was extracted with EtOAc (2×)
  3. washthe combined organic extracts were washed with saturated aqueous NaCl
  4. customdried
  5. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-ef26b15e9b644253a18e4f056967d605
出典データセット
uspto-grants-2006_11
特許番号
US07141669B2

関連ノート

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