2-Methyl-2-butene → 7-[4-(4-Methoxyphenyl)thiazol-2-yl]heptanoic acid

HRID 1616537Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1616537
CC(=CC)C.Cl[O-].[Na+].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:18]=[C:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=[O:29])[S:20][CH:21]=2)=[CH:13][CH:12]=1.P([O-])(O)(O)=[O:31].[K+]>C(O)(C)(C)C.O.C(OCC)(=O)C>[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[N:18]=[C:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:31])=[O:29])[S:20][CH:21]=2)=[CH:15][CH:16]=1

Komponenten

8

Edukt 4

HCID 105532-Methyl-2-buteneHCID 516951Monobasic potassium phosphateHCID 23665760Sodium HypochloriteHCID 593240777-[4-(4-Methoxyphenyl)thiazol-2-yl]heptanal

Produkt 1

HCID 593240787-[4-(4-Methoxyphenyl)thiazol-2-yl]heptanoic acidAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Add 2-methyl-2-butene (7.0 mL) and sodium hypochlorite (2.51 g, 27.75 mmol) to a solution of 7-[4-(4-methoxyphenyl)thiazol-2-yl]heptanal (4.02 g, 13.25 mmol) and potassium dihydrogen phosphate (3.10 g, 22.78 mmol) in tert-butanol (60 mL) and water (12 mL) at room temperature. Stir the mixture for 40 minutes, dilute with ethyl acetate (500 mL) and wash with brine (3×200 mL). Dry the combined organic extracts over sodium sulfate and remove the solvent under reduced pressure. Purify the residue by flash column chromatography on silica gel, eluting with methanol/methylene chloride (1:19), and triturate the residue with hexanes/methylene chloride to afford 7-[4-(4-methoxyphenyl)thiazol-2-yl]heptanoic acid (3.91 g, 88%): APCI MS m/z 320 [C17H21NO3S+H]+.

Aufarbeitung

  1. washwash with brine (3×200 mL)
  2. dry with materialDry the combined organic extracts over sodium sulfate
  3. customremove the solvent under reduced pressure
  4. customPurify the residue by flash column chromatography on silica gel
  5. washeluting with methanol/methylene chloride (1:19)
  6. customtriturate the residue with hexanes/methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-59167aefc3ac472fb1aa1db6446d28fb
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765796B2

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