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

HRID 899310

반응식

HRID 899310 반응식
[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]

참가 물질

4

반응물 2

HCID 587470075-Butyl-pyridine-2-carboxylic acid methoxy-methyl-amideHCID 178418689HCID 178418689, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-902078b39d794527b161f59d8e141b6a
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07354929B2

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