Ethyl 2-hydroxyisobutyrate → 2-Ethoxy-5-(methanesulfonyl)pyridine

HRID 1160726ノート

反応式

HRID 1160726 の反応式
O[C:2]([CH3:9])(C)[C:3]([O:5][CH2:6][CH3:7])=O.CS(C1C=C[C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][N:15]=1)(=O)=O.[H-].[Na+]>CN(C=O)C>[CH2:6]([O:5][C:3]1[CH:2]=[CH:9][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][N:15]=1)[CH3:7]

参加物

5

反応物 3

HCID 6653Ethyl 2-hydroxyisobutyrateHCID 24758Sodium hydrideHCID 131026752,5-Bis(methylsulfonyl)pyridine

生成物 1

HCID 222703272-Ethoxy-5-(methanesulfonyl)pyridine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A mixture of ethyl 2-hydroxyisobutyrate (0.41 mL, 3.0 mmol), 2,5-bis(methyl sulfonyl)pyridine (J. Heterocycl. Chem. 1985, 22, 1583) (0.70 g, 3.0 mmol) and sodium hydride (60% dispersion in mineral oil, 0.14 g, 3.6 mmol) in 30 mL of anhydrous DMF was heated at 80° C. overnight. The reaction mixture was cooled to room temperature, and was partitioned between saturated aqueous ammonium chloride (200 mL) and ether (200 mL). The organic layer was separated and was washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated to dryness, and the residue was purified by flash column chromatography on silica gel eluting with 0 to 80% ethyl acetate in hexane to give the title compound as a 1:1 mixture with 2-ethoxy-5-methylsulfonylpyridine. LC-MS: m/e 288 (M+H)+ (0.70 min).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customwas partitioned between saturated aqueous ammonium chloride (200 mL) and ether (200 mL)
  3. customThe organic layer was separated
  4. washwas washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customthe residue was purified by flash column chromatography on silica gel eluting with 0 to 80% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-28fc9b0b84de40b2b14864399898537d
出典データセット
uspto-grants-2010_10
特許番号
US07816534B2

反応ノート

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