Salicylaldehyde → HCID 69106966、化合物

HRID 132599

反応式

HRID 132599 の反応式
Br[CH2:2][C:3]([C:5]1[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:7][O:8][C:9]=1[CH3:10])=[O:4].[CH:17](=O)[C:18]1[C:19](=[CH:21][CH:22]=[CH:23][CH:24]=1)[OH:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[O:20]1[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[CH:17]=[C:2]1[C:3]([C:5]1[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:7][O:8][C:9]=1[CH3:10])=[O:4]

参加物

5

反応物 3

HCID 6998SalicylaldehydeHCID 11430Potassium CarbonateHCID 27355314-(Bromoacetyl)-5-methyl-3-phenylisoxazole

生成物 1

HCID 69106966HCID 69106966、化合物収率 86%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-(bromoacetyl)-5-methyl-3-phenylisoxazole (commercially available) (140 mg, 0.5 mmol) in DMF (0.5 mL) was added salicylaldehyde (61 mg, 53 μL, 0.5 mmol) followed by potassium carbonate (138 mg, 1.0 mmol) and the resulting mixture stirred vigorously at room temperature for 2 h. The mixture was then poured onto ice-water, and extracted with ethyl acetate. 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 1:1) afforded the title compound (131 mg, 86%) as a white solid. MS m/e: 304.0 [M+H]+.

後処理

  1. additionThe mixture was then poured onto ice-water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were then washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customPurification by chromatography (SiO2, heptane:ethyl acetate:=100:0 to 1:1)

出典と根拠

ORDレコード
ord-4379a3071e2943828002ed1f4588bafc
出典データセット
uspto-grants-2008_06
特許番号
US07388025B2

関連ノート

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