Sodium hydride → 3-Hydroxy-2-methyl-6-nitro-benzoic acid methyl ester

HRID 604279ノート

反応式

HRID 604279 の反応式
[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6](F)[C:5]=1[CH3:14].CS(CCO)(=O)=[O:18].[H-].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([OH:18])[C:5]=1[CH3:14]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 848342-(Methylsulfonyl)ethanolHCID 59849164Methyl 3-fluoro-2-methyl-6-nitrobenzoate

生成物 1

HCID 598492143-Hydroxy-2-methyl-6-nitro-benzoic acid methyl ester収率 89%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirring solution of 3-Fluoro-2-methyl-6-nitro-benzoic acid methyl ester (6 g, 28.2 mmol) and 2-(methylsulfonyl)ethanol (5.2 g, 42.2 mmol) in 47 mL of DMF is added sodium hydride (3.38 g, 84.6 mmol) at 0° C. and the reaction mixture is allowed to warm to room temperature and then stirred for 1.5 hours. The mixture is quenched with 1N HCl solution and partitioned between ethyl acetate. The organic layer is washed with brine and concentrated to dryness and the crude organics purified by flash column chromatography to give 3-Hydroxy-2-methyl-6-nitro-benzoic acid methyl ester (5.3 g) in 89% yields. 1H-NMR (400 MHz, δ, ppm) CDCl3: 2.22 (s, 3H), 3.99 (s, 3H), 6.38 (s, 1H), 6.87 (d, 1H), 7.99 (d, 1H).

後処理

  1. customThe mixture is quenched with 1N HCl solution
  2. custompartitioned between ethyl acetate
  3. washThe organic layer is washed with brine
  4. concentrationconcentrated to dryness
  5. customthe crude organics purified by flash column chromatography

出典と根拠

ORDレコード
ord-497a9922d16848e180bb020cb4b145fb
出典データセット
uspto-grants-2011_03
特許番号
US07910585B2

反応ノート

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