Ethylene Glycol → 2,4-Dichloro-6-(3-[1,3]dioxolan-2-yl-5-methyl-phenoxy)-5-isopropyl-pyrimidine

HRID 426102Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 426102
[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[C:15]([CH3:17])[CH:16]=2)[CH:12]=[O:13])[C:5]([CH:18]([CH3:20])[CH3:19])=[C:4]([Cl:21])[N:3]=1.[CH2:22](O)[CH2:23][OH:24].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.CC(=O)OCC>[Cl:1][C:2]1[N:3]=[C:4]([Cl:21])[C:5]([CH:18]([CH3:19])[CH3:20])=[C:6]([O:8][C:9]2[CH:16]=[C:15]([CH3:17])[CH:14]=[C:11]([CH:12]3[O:24][CH2:23][CH2:22][O:13]3)[CH:10]=2)[N:7]=1

Komponenten

6

Edukt 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 591846443-(2,6-Dichloro-5-isopropyl-pyrimidin-4-yloxy)-5-methyl-benzaldehyde

Produkt 1

HCID 591847212,4-Dichloro-6-(3-[1,3]dioxolan-2-yl-5-methyl-phenoxy)-5-isopropyl-pyrimidineAusbeute 92,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of (6) (1.71 g, 5.25 mmol), ethylene glycol (0.88 ml, 15.75 mmol), and p-toluenesulfonic acid (263 mg, 0.26 mmol) in toluene (20 ml) was refluxed for 3 hr., using a reflux condenser equipped with a Dean-Stark trap. After cooling to room temperature, the mixture was diluted with EA, washed with aqueous saturated sodium bicarbonate solution, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:15)) to afford 1.79 g (92%) of a colorless syrup; 1H NMR (200 MHz, CDCl3) δ 1.40 (6H, d, J=7.0 Hz), 2.40 (3H, s), 3.58 (1H, m), 3.99-4.16 (4H, m), 5.82 (1H, s), 6.92 (1H, s), 7.03 (1H, s), 7.21 (1H, s).

Aufarbeitung

  1. temperaturewas refluxed for 3 hr
  2. customequipped with a Dean-Stark trap
  3. washwashed with aqueous saturated sodium bicarbonate solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:15))

Quellen und Nachweise

ORD-Eintrag
ord-09cff354850d49509f34776bf3ade69a
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106064B2

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