Methyl 6-methylnicotinate 1-oxide → Methyl 6-(acetoxymethyl)nicotinate

HRID 348998노트

반응식

HRID 348998 반응식
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N+:3]=1[O-]>C(OC(=O)C)(=O)C>[C:6]([O:8][CH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1)(=[O:7])[CH3:5]

참가 물질

3

반응물 1

HCID 15883477Methyl 6-methylnicotinate 1-oxide

생성물 1

HCID 10353032Methyl 6-(acetoxymethyl)nicotinate수율 121.2%

시약·촉매·용매 1

HCID 7918Acetic Anhydride용매

실험 절차

To a solution of methyl 6-methylnicotinate (6.05 g) in methylene chloride (100 mL) was added m-chloroperbenzoic acid (77%, 13.5 g). The reaction mixture was stirred at room temperature for 2 h and then diluted with chloroform (100 mL). The mixture was washed successively with aqueous sodium sulfite, saturated sodium bicarbonate, and brine. The organic later was then dried (sodium sulfate), filtered, and concentrated under reduced pressure to provide 6.21 g of methyl 6-methylnicotinate 1-oxide. A solution of methyl 6-methylnicotinate 1-oxide (4.35 g) in acetic anhydride (50 mL) was heated at 120° C. for 2 h and then concentrated under reduced pressure. Purification by flash column chromatography (silica gel, 1:2 to 3:5 ethyl acetate/hexanes) provided 3.3 g of the title compound: 1H NMR (300 MHz, CDCl3) δ 9.18, 8.31, 7.44, 5.29, 3.96, 2.19.

후처리

  1. concentrationconcentrated under reduced pressure
  2. customPurification by flash column chromatography (silica gel, 1:2 to 3:5 ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-aeb2713e5cf54385b03239a355fe75c8
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176242B2

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