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

HRID 14208ノート

反応式

HRID 14208 の反応式
[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]

参加物

3

反応物 1

HCID 15883477Methyl 6-methylnicotinate 1-oxide

生成物 1

HCID 10353032Methyl 6-(acetoxymethyl)nicotinate収率 121.2%

試薬・触媒・溶媒 1

HCID 7918Acetic Anhydride溶媒

実験手順

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: 3H NMR (300 MHz, CDCl3) δ 9.18, 8.31, 7.44, 5.29, 3.96, 2.19.

後処理

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

出典と根拠

ORDレコード
ord-0b398d355f3c42a483894cb1fbd37245
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

反応ノート

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