Toluene → 4-(4-Chloromethyl-2,6-dimethoxyphenoxymethyl)-5-methyl-2-phenyloxazole

HRID 584400Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 584400
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([O:29][CH3:30])[C:14]=1[O:15][CH2:16][C:17]1[N:18]=[C:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:20][C:21]=1[CH3:22])[CH2:10]O.C1(C)C=CC=CC=1>O1CCCC1>[Cl:3][CH2:10][C:9]1[CH:8]=[C:7]([O:6][CH3:5])[C:14]([O:15][CH2:16][C:17]2[N:18]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:20][C:21]=2[CH3:22])=[C:13]([O:29][CH3:30])[CH:12]=1

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 536741583,5-Dimethoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcohol

Produkt 1

HCID 223446054-(4-Chloromethyl-2,6-dimethoxyphenoxymethyl)-5-methyl-2-phenyloxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Thionyl chloride (3.62 g) was added dropwise to a stirred suspension of 3,5-dimethoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcohol (9.00 g) in tetrahydrofuran (50 ml)-toluene (150 ml) at 0° C. After stirring at room temperature for 3 hours, the reaction mixture was concentrated. The residual crystals were dissolved in ethyl acetate and washed with aqueous sodium bicarbonate and water. The ethyl acetate layer was separated, dried (MgSO4), and concentrated to give 4-(4-chloromethyl-2,6-dimethoxyphenoxymethyl)-5-methyl-2-phenyloxazole as crystals. Recrystallization from acetone-hexane gave colorless needles (7.00 g, yield 74%). m.p. 118-119° C.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated
  2. dissolutionThe residual crystals were dissolved in ethyl acetate
  3. washwashed with aqueous sodium bicarbonate and water
  4. customThe ethyl acetate layer was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-89d8354412454290a19492c9c4899874
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06924300B2

Notizen zur Reaktion

Wird geladen…