Perchloric Acid → Methyl 2-(tert-butoxy)-2-(2-phenyl-1,3-thiazol-4-yl)acetate

HRID 590970Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 590970
Cl(O)(=O)(=O)=O.[OH:6][CH:7]([C:12]1[N:13]=[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[S:15][CH:16]=1)[C:8]([O:10][CH3:11])=[O:9]>C(OC(C)(C)C)(=O)C>[C:17]([O:6][CH:7]([C:12]1[N:13]=[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[S:15][CH:16]=1)[C:8]([O:10][CH3:11])=[O:9])([CH3:22])([CH3:18])[CH3:14]

Komponenten

4

Edukt 2

HCID 24247Perchloric AcidHCID 70818588Methyl 2-hydroxy-2-(2-phenyl-1,3-thiazol-4-yl)acetate

Produkt 1

HCID 70818322Methyl 2-(tert-butoxy)-2-(2-phenyl-1,3-thiazol-4-yl)acetateAusbeute 83,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10908tert-Butyl acetateLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, perchloric acid (70%, 4 mL) was added at −10° C. to a solution of methyl 2-hydroxy-2-(2-phenyl-1,3-thiazol-4-yl)acetate (6a) (800 mg, 3.2 mmol) in terbutyl acetate (25 mL). After 1 hour, the reaction was quenched with a saturated solution of sodium bicarbonate (20 mL) and extracted with dichloromethane (2×20 mL). The organic layer was washed with brine (10 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 80/20) to afford the desired product (6b) as a white pale oil (410 mg, 1.34 mmol, 42%).

Aufarbeitung

  1. customthe reaction was quenched with a saturated solution of sodium bicarbonate (20 mL)
  2. extractionextracted with dichloromethane (2×20 mL)
  3. washThe organic layer was washed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 80/20)

Quellen und Nachweise

ORD-Eintrag
ord-9fcc35f547584d4ca6793579ec4017a8
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238026B2

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