Hydrochloric Acid → 1-[3-(4-Bromophenyl)-5-methyl-4-isoxazolyl]ethanone

HRID 132602ノート

反応式

HRID 132602 の反応式
[C:1]([CH2:4][C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2].[O-]CC.[Na+].[Br:12][C:13]1[CH:18]=[CH:17][C:16](/[C:19](/Cl)=[N:20]/O)=[CH:15][CH:14]=1.Cl>CCO>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:4]([C:5](=[O:7])[CH3:6])=[C:1]([CH3:2])[O:3][N:20]=2)=[CH:15][CH:14]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 31261AcetylacetoneHCID 2723922Sodium ethoxideHCID 124408854-Bromo-N-hydroxybenzene-1-carboximidoyl chloride2 回

生成物 1

HCID 212961521-[3-(4-Bromophenyl)-5-methyl-4-isoxazolyl]ethanone収率 84%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

Acetylacetone (1.25 mL, 12 mmol) was added to a sodium ethoxide solution 3.09 N (3.95 mL, 12 mmol) in EtOH (22 mL) at room temperature. The resulting yellow solution was cooled with a ice-bath and a cloudy solution of (E)- and/or (Z)-4-bromo-N-hydroxy-benzenecarboximidoyl chloride (2.35 g, 10 mmol) in EtOH (8 mL) was added dropwise within 10 min keeping the temperature below 5° C. The light yellow suspension was stirred at room temperature for 3 h and then acidified with 6 N HCl and then evaporated. The resulting mixture was extracted with ethyl acetate and the combined organic layers were then washed with water and brine, dried over Na2SO4 and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate:=100:0 to 7:3) afforded the title compound (2.35 g, 84%) as a light yellow oil. MS m/e: 280.1/282.1 [M+H]+.

後処理

  1. temperatureThe resulting yellow solution was cooled with a ice-bath
  2. customthe temperature below 5° C
  3. customevaporated
  4. extractionThe resulting mixture was extracted with ethyl acetate
  5. washthe combined organic layers were then washed with water and brine
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customPurification by chromatography (SiO2, heptane:ethyl acetate:=100:0 to 7:3)

出典と根拠

ORDレコード
ord-1048e235422045e7a2960d2eb01892ff
出典データセット
uspto-grants-2008_06
特許番号
US07388025B2

反応ノート

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