Carbon Dioxide → Mofezolac

HRID 2286277ノート

反応式

HRID 2286277 の反応式
C([Li])CCC.[C:6](=[O:8])=[O:7].CC(C)=O.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:25]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)=[C:24]([CH3:34])[O:23][N:22]=2)=[CH:17][CH:16]=1.C(=O)=O>C1COCC1>[CH3:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[C:25]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)=[C:24]([CH2:34][C:6]([OH:8])=[O:7])[O:23][N:22]=2)=[CH:19][CH:20]=1

参加物

6

反応物 4

HCID 280Carbon DioxideHCID 39549283,4-Bis(4-methoxyphenyl)-5-methylisoxazoleHCID 18522661Acetone cardiceHCID 178418339Butyllithium

生成物 1

HCID 4237Mofezolac

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-75 °C

実験手順

n-Butyllithium (50 ml of 1.6 molar solution, 80 mmole) is added dropwise to a stirred, cold (dry-ice-acetone bath), solution of 3,4-di(p-methoxyphenyl)-5-methylisoxazol (21.72 g., 73.6 mmole, Ex. 2) in THF (220 ml) under a nitrogen atmosphere. After stirring for 1 hour at -75° C., the red coloured mixture is poured into crushed dry-ice and stirred. The stirred mixture is allowed to warm to room temperature, concentrated, and the residue dissolved in water. The resulting solution is twice extracted with ether, layered with ethyl acetate, cooled in ice and acidified with concentrated hydrochloric acid. The layers are separated and the aqueous layer extracted with ethyl acetate. The combined ethyl acetate layers are dried (MgSO4) and concentrated to give a sticky foam residue. Recrystallization from benzene gives the title compound as a colourless solid, m.p. 142°-143° C. The nmr (CDCl3) spectrum τ 6.2 (8H, s, d, CH3O and --CH2 --), 3.28 to 2.52 (8H, m, aryl H's), 0.45 (1H, broad, COOH) agrees with the assignment.

後処理

  1. additionis poured
  2. stirringstirred
  3. temperatureto warm to room temperature
  4. concentrationconcentrated
  5. dissolutionthe residue dissolved in water
  6. extractionThe resulting solution is twice extracted with ether
  7. temperaturecooled in ice
  8. customThe layers are separated
  9. extractionthe aqueous layer extracted with ethyl acetate
  10. dry with materialThe combined ethyl acetate layers are dried (MgSO4)
  11. concentrationconcentrated
  12. customto give a sticky foam residue
  13. customRecrystallization from benzene

出典と根拠

ORDレコード
ord-b9fbfd279bf44af8ba761244478c0d4e
出典データセット
uspto-grants-1982_04
特許番号
US04327222

反応ノート

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