Dimethyl Sulfoxide → 2-Acetyl-6-methylpyridine

HRID 917674

반응식

HRID 917674 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]1[N:17]=[C:16]([CH:18]([OH:20])[CH3:19])[CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:11][C:12]1[N:17]=[C:16]([C:18](=[O:20])[CH3:19])[CH:15]=[CH:14][CH:13]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 3531381-(6-Methylpyridin-2-yl)ethanol

생성물 1

HCID 1388722-Acetyl-6-methylpyridine수율 92%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

반응 조건

온도
-75 °C

실험 절차

To a −75° C. solution of oxalyl chloride (20 mL, 225 mmol, 1.1 equiv) in methylene chloride (300 mL) was slowly added a solution of dimethylsulfoxide (32 mL, 2.2 equiv) in methylene chloride (400 mL) over 1 hour. The resulting solution was stirred at −75° C. for 10 min,and then slowly treated with a solution of 1-(6-methyl-pyridin-2-yl)-ethanol (28 g, 204 mmol, 1 equiv) in methylene chloride (600 mL). The reaction mixture was stirred for 10 min at the same temperature, and then slowly treated with triethylamine (140 mL, 1.02 mol, 5 equiv). The resulting mixture was warmed to 20° over 2 hours, and then quenched with water (500 mL). The organic phase was separated, dried over magnesium sulfate and concentrated in vacuo to yield the crude material. Silica gel chromatography (3:1 hexanes/ethyl acetate) yielded 1-(6-Methyl-pyridin-2-yl)-ethanone (25.36 g, 92%).

후처리

  1. stirringThe reaction mixture was stirred for 10 min at the same temperature
  2. temperatureThe resulting mixture was warmed to 20° over 2 hours
  3. customquenched with water (500 mL)
  4. customThe organic phase was separated
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto yield the crude material

출처 및 근거

ORD 기록
ord-5928362ea2f2426dbbf9f14fcd235798
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07273936B2

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