Nitromethane → HCID 9888784, Verbindung

HRID 988008Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 988008
[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 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

110 mg (0.2.9 mmol) of 3,4-di(t-butyldimethylsiloxy)benzaldehyde was dissolved in 10 ml of THF under the atmosphere of argon at −40° C., and 0.32 ml of rare earth metal complex solution A0 was mixed into the solution. After stirring for 30 minutes, 88.5 mg (1.45 mmol) of nitromethane was added dropwise to the mixture. After 67-hour reaction: time, (R)-1-(3,4-di(t-butyldimethylsiloxy)phenyl)-2-nitroethanol with an optical purity of 92% e.e. was obtained in a yield of 74%.

Aufarbeitung

  1. customAfter 67-hour reaction

Quellen und Nachweise

ORD-Eintrag
ord-479f47e5b98f4d2aab322617809413d3
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06632955B1

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