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

HRID 604279노트

반응식

HRID 604279 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-497a9922d16848e180bb020cb4b145fb
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910585B2

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