1-Bromooctane → (s)-2-[4-n-Octyloxyphenyl]-5-[6-methyloctyl]pyrimidine

HRID 4454

Reaktionsgleichung

Reaktionsgleichung von HRID 4454
[H-].[Na+].[CH3:3][C@@H:4]([CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][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.Br[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>CN(C)C=O>[CH2:26]([O:22][C:19]1[CH:20]=[CH:21][C:16]([C:13]2[N:12]=[CH:11][C:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C@@H:4]([CH3:3])[CH2:23][CH3:24])=[CH:15][N:14]=2)=[CH:17][CH:18]=1)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Komponenten

5

Edukt 3

HCID 81401-BromooctaneHCID 24758Sodium hydrideHCID 136393723(s)-4-[5-(6-Methyl octyl)-2-pyrimidinyl]phenol

Produkt 1

HCID 18611622(s)-2-[4-n-Octyloxyphenyl]-5-[6-methyloctyl]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Pour 0.33 g of sodium hydride (about 50% oil suspension), 3 ml of dry N,N-dimethylformamide into a 30 ml three-mouth flask equipped with a cooling tube, thermometer, dripping funnel, and calcium chloride tube. Next, slowly drip 1.71 g of optically active (s)-4-[5-(6-methyl octyl)-2-pyrimidinyl]phenol which is dissolved in 6 ml of dry N,N-dimethylformamide, into the flask at room temperature. Furthermore, after reacting it for 30 minutes, add 1.10 g of 1-bromoctane, allow to react for 7 hours at 90° C. After the reaction, pour the mixture into ice water, then extract the product with ethyl acetate. The organic layer is thoroughly washed with water, dried, the organic solvent is evaporated and removed, and then the impure product is obtained. This impure product is refined with silica gel chromatography, and recrystallized to obtain 1.3 g of optically active (s)-2-[4-n-octyloxyphenyl]-5-[6-methyloctyl]pyrimidine.

Aufarbeitung

  1. customequipped with a cooling tube
  2. customfor 30 minutes
  3. customto react for 7 hours at 90° C
  4. customAfter the reaction
  5. extractionextract the product with ethyl acetate
  6. washThe organic layer is thoroughly washed with water
  7. customdried
  8. customthe organic solvent is evaporated
  9. customremoved
  10. customthe impure product is obtained
  11. customrecrystallized

Quellen und Nachweise

ORD-Eintrag
ord-ae7c4249e17a4e4bb669f0513f28a2f7
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04725688

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