Triethylamine → 4,4-Difluoro-3-methyl-3-butenyl 2-(4-chlorobutoxy)-4-methylpyrimidine-5-carboxylate

HRID 917380

Reaktionsgleichung

Reaktionsgleichung von HRID 917380
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6].CS([C:11]1[N:16]=[C:15]([CH3:17])[C:14]([C:18]([O:20][CH2:21][CH2:22][C:23]([CH3:27])=[C:24]([F:26])[F:25])=[O:19])=[CH:13][N:12]=1)(=O)=O.C(N(CC)CC)C>O>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:11]1[N:16]=[C:15]([CH3:17])[C:14]([C:18]([O:20][CH2:21][CH2:22][C:23]([CH3:27])=[C:24]([F:26])[F:25])=[O:19])=[CH:13][N:12]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 135694-Chloro-1-butanolHCID 691816824,4-Difluoro-3-methyl-3-butenyl 2-methanesulfonyl-4-methylpyrimidine-5-carboxylate

Produkt 1

HCID 230202154,4-Difluoro-3-methyl-3-butenyl 2-(4-chlorobutoxy)-4-methylpyrimidine-5-carboxylateAusbeute 27,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To 1.02 g (9.4 mmol) of 4-chlorobutanol was dissolved 1.00 g (3.1 mmol) of 4,4-difluoro-3-methyl-3-butenyl 2-methanesulfonyl-4-methylpyrimidine-5-carboxylate, followed by the addition of 0.38 g (3.8 mmol) of triethylamine under ice-cooling and stirring at room temperature for 14 hours. The reaction liquid was then poured in water and extracted with diethyl ether. The organic layer was washed with water and a saturated saline solution in this order, followed by drying over anhydrous magnesium sulfate and concentration under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:9) to obtain 0.30 g (yield: 27%) of 4,4-difluoro-3-methyl-3-butenyl 2-(4-chlorobutoxy)-4-methylpyrimidine-5-carboxylate.

Aufarbeitung

  1. temperaturecooling
  2. customThe reaction liquid
  3. extractionextracted with diethyl ether
  4. washThe organic layer was washed with water
  5. dry with materialby drying over anhydrous magnesium sulfate and concentration under reduced pressure
  6. customThe residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:9)

Quellen und Nachweise

ORD-Eintrag
ord-de013e0968cf4bff925e867421243f82
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07273878B2

Verknüpfte Notizen

Wird geladen…