Sodium Hypochlorite → Methyl 3-chloro-1-methyl-1H-pyrazole-5-carboxylate

HRID 402485

反応式

HRID 402485 の反応式
[Cl:1][C:2]1[CH2:6][CH:5]([C:7]([O:9][CH3:10])=[O:8])[N:4]([CH3:11])[N:3]=1.Cl[O-].[Na+]>>[Cl:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:4]([CH3:11])[N:3]=1

参加物

3

反応物 2

HCID 23665760Sodium HypochloriteHCID 67209560methyl 3-chloro-1-methyl-4,5-dihydro-1H-pyrazole-5-carboxylate

生成物 1

HCID 67209478Methyl 3-chloro-1-methyl-1H-pyrazole-5-carboxylate収率 29%

実験手順

Methyl 3-chloro-1-methyl-4,5-dihydro-1H-pyrazole-5-carboxylate (21 g, 119 mmol) was added drop wise to sodium hypochlorite (95 ml, 155 mmol) under ice cooling. Then, the ice bath was removed and stirring continued for 72 h. The organic phase was separated, washed with Na2S2O3 (10% aqueous solution) and water, dried over Na2SO4 and the solvent removed under reduced pressure. The resulting oil was purified by distillation (bp 35° C., 0.2 mbar) followed by column chromatography (eluent 80% hexane in EtOAc) to yield 6.0 g (29%) of the title compound. [1H-NMR (DMSO-d6, 360 MHz) δ 6.96 (s, 1H), 6.80 (s, 1H), 4.07 (s, 3H), 3.86 (s, 3H)]

後処理

  1. customThen, the ice bath was removed
  2. customThe organic phase was separated
  3. washwashed with Na2S2O3 (10% aqueous solution) and water
  4. dry with materialdried over Na2SO4
  5. customthe solvent removed under reduced pressure
  6. distillationThe resulting oil was purified by distillation (bp 35° C., 0.2 mbar)

出典と根拠

ORDレコード
ord-d78d5c7e05f141409e00285f612019ff
出典データセット
uspto-grants-2014_06
特許番号
US08742106B2

関連ノート

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