Sodium Bicarbonate → 2-Chloro-1-(5-(2,6-difluorophenyl)-4,5-dihydroisoxazol-3-yl)ethan-1-one

HRID 75183ノート

反応式

HRID 75183 の反応式
[Cl:1][CH2:2][C:3](=[O:8])[C:4](Cl)=[N:5][OH:6].[CH:9]([C:11]1[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=1[F:18])=[CH2:10].C(=O)(O)[O-].[Na+]>C(#N)C>[Cl:1][CH2:2][C:3]([C:4]1[CH2:10][CH:9]([C:11]2[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=2[F:18])[O:6][N:5]=1)=[O:8]

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 27783002,6-DifluorostyreneHCID 68330913-chloro-N-hydroxy-2-oxopropanimidoyl chloride

生成物 1

HCID 866744762-Chloro-1-(5-(2,6-difluorophenyl)-4,5-dihydroisoxazol-3-yl)ethan-1-one収率 74.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a stirred solution of 3-chloro-N-hydroxy-2-oxopropanimidoyl chloride (0.89 g, 5.71 mmol) in acetonitrile (20 mL) was added 2-ethenyl-1,3-difluorobenzene (1.0 g, 7.14 mmol) and sodium bicarbonate (1.8 g, 2.14 mmol) at room temperature. The reaction mixture was stirred at room temperature for 12 h, concentrated in under reduced pressure and the resulting material was partitioned between ethyl acetate (50 mL) and water (50 mL). The organic layer was separated, washed with saturated aqueous sodium chloride solution and concentrated in under reduced pressure. The resulting material was triturated with petroleum ether and filtered to provide the title product as white solid (1.1 g) melting at 82.1-83.4° C.

後処理

  1. concentrationconcentrated in under reduced pressure
  2. customthe resulting material was partitioned between ethyl acetate (50 mL) and water (50 mL)
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous sodium chloride solution
  5. concentrationconcentrated in under reduced pressure
  6. customThe resulting material was triturated with petroleum ether
  7. filtrationfiltered

出典と根拠

ORDレコード
ord-58f7c26fe9144f4a865466c1ccbdc436
出典データセット
uspto-grants-2014_09
特許番号
US08835427B2

反応ノート

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