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Acetic Acid → 5-Octyloxy-2-(p-hydroxyphenyl)pyrimidine (+)-4-(1-hexyloxy-2,2,2-trifluoroethyl)benzoate

HRID 1728429
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HRID 1728429 반응식
[CH2:1]([O:9][C:10]1[CH:11]=[N:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[N:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].N1(C2C=CN=CC=2)CCCC1.C1(N=C=NC2CCCCC2)CCCCC1.C(O)(=O)C.[CH2:53]([O:59][CH:60]([C:65]1[CH:73]=[CH:72][C:68]([C:69]([OH:71])=[O:70])=[CH:67][CH:66]=1)[C:61]([F:64])([F:63])[F:62])[CH2:54][CH2:55][CH2:56][CH2:57][CH3:58]>ClCCl>[CH2:53]([O:59][CH:60]([C:65]1[CH:73]=[CH:72][C:68]([C:69]([OH:71])=[O:70])=[CH:67][CH:66]=1)[C:61]([F:63])([F:64])[F:62])[CH2:54][CH2:55][CH2:56][CH2:57][CH3:58].[CH2:1]([O:9][C:10]1[CH:15]=[N:14][C:13]([C:16]2[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=2)=[N:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 10868DicyclohexylcarbodiimideHCID 755674-PyrrolidinopyridineHCID 19018076(+)-4-(1-Hexyloxy-2,2,2-trifluoroethyl)benzoic acidHCID 135708811Phenol, 4-[5-(octyloxy)-2-pyrimidinyl]-

생성물 1

HCID 1363784075-Octyloxy-2-(p-hydroxyphenyl)pyrimidine (+)-4-(1-hexyloxy-2,2,2-trifluoroethyl)benzoate
수율 81%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In 20 ml of dry dichloromethane were dissolved 3.04 g (10 millimoles) of optically active (+)-4-(1-hexyloxy-2,2,2-trifluoroethyl)benzoic acid, 3.00 g (10 millimoles) of 5-octyloxy-2-(p-hydroxyphenyl)pyrimidine and 0.2 g of 4-pyrrolidinopyridine. Then, 2.5 g (12 millimoles) of dicyclohexylcarbodiimide was added and the resulting mixture was stirred at room temperature for 6 hours. After the reaction, 5% aqueous solution of acetic acid was added and the whole was extracted with dichloromethane. The organic layer was washed successively with water and 7% aqueous solution of sodium hydrogen carbonate and dried on anhydrous magnesium sulfate, and then the solvent was distilled off and the residue was purified by silica gel column chromatography. Thus, 4.75 g (yield 81%) of optically active 5-octyloxy-2-(p-hydroxyphenyl)pyrimidine (+)-4-(1-hexyloxy-2,2,2-trifluoroethyl)benzoate was obtained. ##STR8##

후처리

  1. additionwas added
  2. extractionthe whole was extracted with dichloromethane
  3. washThe organic layer was washed successively with water and 7% aqueous solution of sodium hydrogen carbonate
  4. dry with materialdried on anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-f2408dd5f5954a3eac469637d10d8039
출처 데이터셋
uspto-grants-1994_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05326871

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