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

HRID 861085

반응식

HRID 861085 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 114357761-(2-Methylphenyl)-2-(4-pyridyl)ethanone수율 67%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0e724bcb863a4d3982f7d3d426798aba
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153959B2

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