Nonanoyl chloride → 4-(4-Nonanoyloxy-5,5,5-trifluoro-1-pentyl)phenyl-5-decyloxypyrimidine

HRID 1735984

Reaktionsgleichung

Reaktionsgleichung von HRID 1735984
[OH:1][CH:2]([C:29]([F:32])([F:31])[F:30])[CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:14][N:13]=2)=[CH:8][CH:7]=1.[C:33](Cl)(=[O:42])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>N1C=CC=CC=1.C1(C)C=CC=CC=1>[C:33]([O:1][CH:2]([C:29]([F:31])([F:32])[F:30])[CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[N:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:14][N:13]=2)=[CH:10][CH:11]=1)(=[O:42])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

Komponenten

5

Edukt 2

HCID 69819Nonanoyl chlorideHCID 19694914(-)-2-(4-(4-Hydroxy-5,5,5-trifluoro-1-pentyl)phenyl)-5-decyloxypyrimidine

Produkt 1

HCID 867496554-(4-Nonanoyloxy-5,5,5-trifluoro-1-pentyl)phenyl-5-decyloxypyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

1.1 g (2.5 mmol) of (-)-2-(4-(4-hydroxy-5,5,5-trifluoro-1-pentyl)phenyl)-5-decyloxypyrimidine was dissolved in 10 ml of pyridine, followed by addition of 0.53 g (3 mmol) of nonanoyl chloride and 2-hour reaction at 20°-30° C. The reaction mixture was diluted with 100 ml of toluene, and the toluene layer was washed with 4N hydrochloric acid, water, a 5% sodium bicarbonate solution and water successively in that order and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using toluene/ethyl acetate as eluent to obtain 1.25 g of (+)-2-(4-(4-nonanoyloxy-5,5,5-trifluoro-1-pentyl)phenyl-5-decyloxypyrimidine.

Aufarbeitung

  1. washthe toluene layer was washed with 4N hydrochloric acid, water
  2. concentrationa 5% sodium bicarbonate solution and water successively in that order and concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f0dd5e27fb014629acbc5370acbff31f
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05539115

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