Nitromethane → HCID 9888784, Verbindung

HRID 988009Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 988009
[O:1]([C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH:12]=[O:13])[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[N+:25]([CH3:28])([O-:27])=[O:26]>C1COCC1>[O:1]([C:9]1[CH:10]=[C:11]([C@@H:12]([OH:13])[CH2:28][N+:25]([O-:27])=[O:26])[CH:14]=[CH:15][C:16]=1[O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:19])[CH3:20])[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3]

Komponenten

4

Edukt 2

HCID 6375NitromethaneHCID 109374483,4-di(t-butyldimethylsiloxy)benzaldehyde

Produkt 1

HCID 9888784HCID 9888784, VerbindungAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

105 mg (0.28 mmol) of 3,4-di(t-butyldimethylsiloxy)benzaldehyde was dissolved in 10 ml of THF under the atmosphere of argon at −40° C., and 0.31 ml of rare earth metal complex solution D1 was mixed into the solution. After stirring for 30 minutes, 85.5 mg (1.40mmol) of nitromethane was added dropwise to the mixture. After 61-hour reaction time, (R)-1-(3,4-di(t-butyldimethylsilxy)phenyl)-2-nitroethanol with an optical purity of 87% e.e. was obtained in a yield of 86%.

Aufarbeitung

  1. customwas obtained in a yield of 86%

Quellen und Nachweise

ORD-Eintrag
ord-27ddb4b3f2fa4b5591d7c688db2a325c
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06632955B1

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