Imidazole → (Dimethoxyphosphinyl)[[(1,1-dimethylethyl)dimethylsilyl]oxy]acetic acid (4-nitrophenyl)methyl ester

HRID 1290393

Reaktionsgleichung

Reaktionsgleichung von HRID 1290393
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12](=[O:21])[CH:13]([P:15]([O:19][CH3:20])([O:17][CH3:18])=[O:16])[OH:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].CN(C)C=O.[Si:27](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28].N1C=CN=C1>C(OCC)(=O)C.C(OCC)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12](=[O:21])[CH:13]([P:15]([O:19][CH3:20])([O:17][CH3:18])=[O:16])[O:14][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 10064522Acetic acid, (dimethoxyphosphinyl)hydroxy-, (4-nitrophenyl)methyl ester

Produkt 1

HCID 9932571(Dimethoxyphosphinyl)[[(1,1-dimethylethyl)dimethylsilyl]oxy]acetic acid (4-nitrophenyl)methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584169Diethylether ethylacetateLösungsmittel

Versuchsvorschrift

To a mixture of 3.48 g of product from Example 97 and 12 ml of dimethylformamide is added 1.86 g of t-butyldimethylsilyl chloride and 1.86 g of imidazole. After stirring the reaction at room temperature for 2 hours, the mixture is diluted with 50% ethyl acetate/diethyl ether, washed 5 times with water, once with saturated sodium bicarbonate and once with saturated sodium chloride. The organic layer is dried, filtered and concentrated in vacuo to give 3.90 g of the desired silylated product.

Aufarbeitung

  1. customthe reaction at room temperature for 2 hours
  2. washwashed 5 times with water
  3. customThe organic layer is dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give 3.90 g of the desired silylated product

Quellen und Nachweise

ORD-Eintrag
ord-393c0b151ecb48a3a1be8a0dcbdc35c0
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750735

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