Water → Methyl 4-[5-methyl-4-(sulfanylmethyl)-1,3-oxazol-2-yl]benzoate

HRID 1526859

Reaktionsgleichung

Reaktionsgleichung von HRID 1526859
C([S:4][CH2:5][C:6]1[N:7]=[C:8]([C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=2)[O:9][C:10]=1[CH3:11])(=O)C.C(=O)([O-])[O-].[K+].[K+].O>CO>[CH3:11][C:10]1[O:9][C:8]([C:12]2[CH:13]=[CH:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:20][CH:21]=2)=[N:7][C:6]=1[CH2:5][SH:4]

Komponenten

5

Edukt 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 86709133Methyl 4-[4-[(acetylsulfanyl)methyl]-5-methyl-1,3-oxazol-2-yl]benzoate

Produkt 1

HCID 86709134Methyl 4-[5-methyl-4-(sulfanylmethyl)-1,3-oxazol-2-yl]benzoateAusbeute 102,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of methyl 4-[4-[(acetylsulfanyl)methyl]-5-methyl-1,3-oxazol-2-yl]benzoate (4.29 g, 14.05 mmol, 1.00 equiv) and potassium carbonate (4.85 g, 34.84 mmol, 3.00 equiv) in methanol (50 mL) was stirred at 35° C. under an inert atmosphere of nitrogen for 30 min Water (100 mL) was then added and the resulting solution was extracted with 3×150 mL of dichloromethane. The combined organic layers was washed with 2×300 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to yield 3.8 g of crude methyl 4-[5-methyl-4-(sulfanylmethyl)-1,3-oxazol-2-yl]benzoate as a white solid. LC-MS: (ES, m/z): 305 [M+CH3CN+H]+, 264 [M+H]+, 230.

Aufarbeitung

  1. additionwas then added
  2. extractionthe resulting solution was extracted with 3×150 mL of dichloromethane
  3. washThe combined organic layers was washed with 2×300 mL of brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-91945b91a15e4f3faa3d330178342ef7
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085570B2

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