Oxalic Acid → HCID 67597547, 화합물

HRID 1600989노트

반응식

HRID 1600989 반응식
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

참가 물질

9

반응물 4

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

생성물 1

HCID 67597547HCID 67597547, 화합물

시약·촉매·용매 4

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 5234Sodium Chloride용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-eba4dde1170c4346b319150726329b9c
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05977105

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