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Methanol → 4-Methyl-2-(4-trifluoromethyl-phenyl)-oxazole-5-carboxylic acid methyl ester

HRID 860596
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 860596
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:16]=[CH:15][C:6]([C:7]([NH:9][CH:10]([CH3:14])[C:11]([OH:13])=O)=O)=[CH:5][CH:4]=1.[C:19](Cl)(=[O:23])C(Cl)=O.C(N(CC)CC)C.[CH3:32][OH:33]>CN(C=O)C>[CH3:32][O:33][C:19]([C:11]1[O:13][C:7]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:17])[F:18])=[CH:16][CH:15]=2)=[N:9][C:10]=1[CH3:14])=[O:23]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 887MethanolHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 21942791HCID 21942791, Verbindung

Produkt 1

HCID 592122174-Methyl-2-(4-trifluoromethyl-phenyl)-oxazole-5-carboxylic acid methyl esterAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Katalysator

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-(4-Trifluoromethyl-benzoylamino)-propionic acid (33.4 g, 128 mmol) is added oxalyl chloride (111 mL, 1.27 Mol) and 1 drop of DMF and the solution stirred overnight. The volatiles are removed in vacuo and toluene (20 mL) is added. The toluene is then removed in vacuo. To the resultant crude oil is dissolve in 50 mL methylene chloride, cooled to 0° C. and triethylamine (27 mL, 192 mmol) is added followed by methanol (50 mL). After 3 hrs the volatiles are removed in vacuo and the crude oil is purified by flash column chromatography (20%–50% ethyl acetate/hexanes) to provide 12.6 g (35%) of 4-Methyl-2-(4-trifluoromethyl-phenyl)-oxazole-5-carboxylic acid methyl ester. This ester (2.0 g, 7.0 mmol) is reduced to the alcohol by dissolution in THF (50 mL) and adding 4 eq. LiBH4 (0.610 g, 28.0 mmol) to provide 1.8 g (100%) [4-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-methanol. MS M++1 258.

Aufarbeitung

  1. customThe volatiles are removed in vacuo and toluene (20 mL)
  2. additionis added
  3. customThe toluene is then removed in vacuo
  4. dissolutionTo the resultant crude oil is dissolve in 50 mL methylene chloride
  5. customAfter 3 hrs the volatiles are removed in vacuo
  6. customthe crude oil is purified by flash column chromatography (20%–50% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-78a4de7190ee4728b1fd03073217b053
Quelldatensatz
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07153878B2

Notizen zur Reaktion

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