Water → 2-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-thiazole-5-carboxylic acid ethyl ester

HRID 1923639Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1923639
[H-].[Na+].[CH3:3][C:4]1[O:8][N:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]=1[CH2:15][OH:16].[CH2:17]([O:19][C:20]([C:22]1[S:26][C:25](Cl)=[N:24][CH:23]=1)=[O:21])[CH3:18].O>O1CCCC1>[CH2:17]([O:19][C:20]([C:22]1[S:26][C:25]([O:16][CH2:15][C:5]2[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[N:7][O:8][C:4]=2[CH3:3])=[N:24][CH:23]=1)=[O:21])[CH3:18]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2776149(5-Methyl-3-phenyl-1,2-oxazol-4-yl)methanolHCID 19017727Ethyl 2-chloro-1,3-thiazole-5-carboxylate

Produkt 1

HCID 595684942-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-thiazole-5-carboxylic acid ethyl esterAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred suspension of sodium hydride (304 mg, 6.98 mmol, 60% dispersion in mineral oil) in tetrahydrofuran (30 mL) at 0° C. under argon was added (5-methyl-3-phenyl-isoxazol-4-yl)-methanol (1.0 g, 5.28 mmol) The mixture was warmed to room temperature and after 1 h the reaction mixture was cooled to 0° C. then a solution of 2-chloro-thiazole-5-carboxylic acid ethyl ester (1.01 g, 5.28 mmol) in THF (15 mL) added. The reaction mixture was warmed to room temperature and after 15 h, water (20 mL) was added and the resulting mixture extracted with ethyl acetate. The combined organic extracts were dried, filtered and concentrated. Purification by chromatography (silica, 20% ethyl acetate in heptane) gave the title compound (940 mg, 52% yield) as an off-white solid. MS: m/e=345.0 [M+H]+.

Aufarbeitung

  1. temperaturewas cooled to 0° C.
  2. temperatureThe reaction mixture was warmed to room temperature and after 15 h
  3. extractionthe resulting mixture extracted with ethyl acetate
  4. customThe combined organic extracts were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by chromatography (silica, 20% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-e204716e625e4753843b7c04b8808360
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178522B2

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