Benzoic acid, 3-methyl-, methyl ester → 1-(2-Methylphenyl)-2-(4-pyridyl)ethanone

HRID 861085

反応式

HRID 861085 の反応式
C[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7]C)=O.[N:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1.[C:19](=O)(O)[O-].[Na+]>O1CCCC1>[C:3]1([CH3:19])[CH:2]=[CH:11][CH:10]=[CH:9][C:4]=1[C:5](=[O:7])[CH2:18][C:15]1[CH:16]=[CH:17][N:12]=[CH:13][CH:14]=1

参加物

5

反応物 3

HCID 7435Benzoic acid, 3-methyl-, methyl esterHCID 79634-MethylpyridineHCID 516892Sodium Bicarbonate

生成物 1

HCID 114357761-(2-Methylphenyl)-2-(4-pyridyl)ethanone収率 67%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Methyl 3-methylbenzoate (6.0 g, 40 mmol), tetrahydrofuran (50 mL), and 4-picoline (4.1 g, 44 mmol) were stirred at −78° C. under an atmosphere of nitrogen. Sodium (bis)trimethylsilylamide 1.0 M in tetrahydrofuran (88 mL, 88 mmol) was added dropwise. The mixture was allowed to warm to room temperature, stirred for 16 hours and then was poured into saturated aqueous sodium bicarbonate solution. The mixture was then extracted with ethyl acetate (3×50 mL). The combined organics were washed with brine (2×50 mL), dried over magnesium sulfate, and concentrated. The product was recrystallized from ethyl acetate/hexane to yield a light yellow solid (5.7 g, 67%), mp 118.0–119.0° C.; 1H NMR (acetone-d6/300 MHz) 8.50 (m, 2H), 7.90 (m, 2H), 7.44 (m, 2H), 7.29 (m, 2H), 4.45 (s, 2H), 2.41 (s, 3H); ESHRMS m/z 212.1067 (M+H, C14H13NO requires 212.1075); Anal. Calc'd for C14H13NO: C, 79.59; H, 6.20; N, 6.63. Found: C, 79.54; H, 6.30; N, 6.56.

後処理

  1. extractionThe mixture was then extracted with ethyl acetate (3×50 mL)
  2. washThe combined organics were washed with brine (2×50 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe product was recrystallized from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-0e724bcb863a4d3982f7d3d426798aba
出典データセット
uspto-grants-2006_12
特許番号
US07153959B2

関連ノート

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