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

HRID 1728429Notes

Reaction equation

HRID 1728429 reaction equation
[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]

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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##

Workup

  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

Sources & evidence

ORD record
ord-f2408dd5f5954a3eac469637d10d8039
Source dataset
uspto-grants-1994_07
Patent number
US05326871

Reaction notes

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