Oxalic Acid → HCID 67597547、化合物

HRID 1600989ノート

反応式

HRID 1600989 の反応式
C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC(S([O:16][CH2:17][C:18]23[CH2:25][CH2:24][CH:21]([CH2:22][CH2:23]2)[CH2:20][CH2:19]3)(=O)=O)=CC=1.O[C:28]1[CH:45]=[CH:44][C:31]([O:32][CH2:33][CH:34]([OH:43])[CH2:35][CH2:36][C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=2)=[CH:30][CH:29]=1.[C:46]([OH:51])(=[O:50])[C:47]([OH:49])=[O:48]>CN(C)C=O.[Cl-].[Na+].CCOCC.O>[C:46]([OH:51])(=[O:50])[C:47]([OH:49])=[O:48].[C:18]12([CH2:17][O:16][C:28]3[CH:45]=[CH:44][C:31]([O:32][CH2:33][CH:34]([OH:43])[CH2:35][CH2:36][C:37]4[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=4)=[CH:30][CH:29]=3)[CH2:19][CH2:20][CH:21]([CH2:22][CH2:23]1)[CH2:24][CH2:25]2

参加物

9

反応物 4

HCID 971Oxalic AcidHCID 11430Potassium CarbonateHCID 280185Bicyclo[2.2.2]oct-1-ylmethyl 4-methylbenzene-1-sulfonateHCID 21830741HCID 21830741、化合物

生成物 1

HCID 67597547HCID 67597547、化合物

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 5234Sodium Chloride溶媒HCID 6228Dimethylformamide溶媒

実験手順

Anhydrous potassium carbonate (0.100 g) was added to a solution of bicyclo[2,2,2]oct-1-ylmethyl para-toluenesulfonate (0.180 g) and (±)-1-(4-hydroxyphenoxy)-4-(3-pyridyl)-2-butanol (0.115 g) in anhydrous dimethylformamide (3 ml). The mixture was heated at reflux under nitrogen, with stirring for 6 hours then cooled to room temperature before being poured into water (20 ml). The mixture was diluted with saturated aqueous sodium chloride solution (20 ml) and extracted with ethyl acetate (2×30 ml). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with acetone:hexane (2:3) to give an oil. This oil was treated with oxalic acid (excess) in ether to give the title compound as a solid (0.167 g) which was recrystallised from ethyl acetate.

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux under nitrogen
  3. extractionextracted with ethyl acetate (2×30 ml)
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography over silica eluting with acetone:hexane (2:3)
  8. customto give an oil

出典と根拠

ORDレコード
ord-eba4dde1170c4346b319150726329b9c
出典データセット
uspto-grants-1999_11
特許番号
US05977105

反応ノート

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