tert-Butyl hydroperoxide → 1H-Indene-2-carboxylic acid, 5-chloro-2,3-dihydro-2-hydroxy-1-oxo-, methyl ester

HRID 547987

Reaktionsgleichung

Reaktionsgleichung von HRID 547987
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH:6]([C:12]([O:14][CH3:15])=[O:13])[CH2:5]2.C([O:20]O)(C)(C)C>C1(C)C=CC=CC=1.C(#N)C.CC(C)[O-].[Zr+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[C:6]([OH:20])([C:12]([O:14][CH3:15])=[O:13])[CH2:5]2

Komponenten

6

Edukt 2

HCID 6410tert-Butyl hydroperoxideHCID 110423911H-Indene-2-carboxylic acid, 5-chloro-2,3-dihydro-1-oxo-, methyl ester3×

Produkt 1

HCID 109775851H-Indene-2-carboxylic acid, 5-chloro-2,3-dihydro-2-hydroxy-1-oxo-, methyl esterAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3083750Zirconium(4+) propan-2-olateKatalysatorHCID 1140TolueneLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

To a solution of methyl 5-chloro-2,3-dihydro-1-oxo-1H-indene-2-carboxylate (also known as methyl 5-chloro-1-oxo-2,3-dihydroindene-2-carboxylate) (0.500 g, 2.23 mmol) (Formula IIa wherein R1 is OCH3 and R4 is Cl) and zirconium(1V) isopropoxide (0.0086 g, 0.022 mmol) in toluene (1.34 g, 1.56 mL) at 30° C. was added an aqueous solution of tert-butyl hydroperoxide (70%, 0.316 g, 2.46 mmol). The reaction mixture was stirred for 24 hours at 30° C. and then diluted with acetonitrile (about 6 mL). Quantitative HPLC analysis showed 92% conversion of methyl 5-chloro-2,3-dihydro-1-oxo-1H-indene-2-carboxylate, forming racemic methyl 5-chloro-2,3-dihydro-2-hydroxy-1-oxo-1H-indene-2-carboxylate in 89% yield (97% chemoselectivity).

Aufarbeitung

  1. customat 30° C.

Quellen und Nachweise

ORD-Eintrag
ord-4932bb66191d4e22ae50ef1098387465
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07939685B2

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