Thionyl Chloride → Ethyl 2-[4-(chloromethyl)phenyl]-1,3-oxazole-4-carboxylate

HRID 1716825Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1716825
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][CH:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=2)=[CH:9][CH:8]=1>C(Cl)Cl>[Cl:3][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][CH:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=2)=[CH:9][CH:8]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 46834789Ethyl 2-[4-(hydroxymethyl)phenyl]-1,3-oxazole-4-carboxylate

Produkt 1

HCID 46834790Ethyl 2-[4-(chloromethyl)phenyl]-1,3-oxazole-4-carboxylateAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of methylene chloride at −10° C. and excess thionyl chloride was added portionwise ethyl 2-[4-(hydroxymethyl)phenyl]-1,3-oxazole-4-carboxylate (1 eq) and the resulting mixture was stirred at room temperature for 3 h. The solvent was removed and the residue was azeotroped with toluene, dissolved in methylene chloride, washed with aqueous sodium bicarbonate, dried over magnesium sulfate, filtered and evaporated to give a yield of 96% of the product as white crystals; m.p. 115-117° C. 1H NMR (300 MHz, CDCl3, δ): 8.28 (s, 1H), 8.12 (d, 2H, J=8.5 Hz), 7.50 (d, 2H, J=8.5 Hz), 4.62 (s, 2H), 4.43 (m, 2H, J=7.4 Hz), 1.41 (t, 3H, J=7.4 Hz).

Aufarbeitung

  1. customThe solvent was removed
  2. customthe residue was azeotroped with toluene
  3. dissolutiondissolved in methylene chloride
  4. washwashed with aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c2042fb571624d4381a6a957afff6cec
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803825B2

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