Imidazole → (E)-3-[2(tert-Butyl-dimethyl-silanoxy)-phenyl]-acrylic acid

HRID 655077

Reaktionsgleichung

Reaktionsgleichung von HRID 655077
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11].[CH3:13][C:14]([Si:17](Cl)([CH3:19])[CH3:18])([CH3:16])[CH3:15].N1C=CN=C1.[Li+].[OH-]>CN(C=O)C.C1COCC1.O>[C:14]([Si:17]([CH3:19])([CH3:18])[O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11])([CH3:16])([CH3:15])[CH3:13]

Komponenten

7

Edukt 4

HCID 795ImidazoleHCID 3939Lithium HydroxideHCID 28928tert-Butyldimethylsilyl chlorideHCID 637540O-Coumaric Acid

Produkt 1

HCID 22290462(E)-3-[2(tert-Butyl-dimethyl-silanoxy)-phenyl]-acrylic acidAusbeute 53,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

To a solution of 8.2 g of (E)-3-(2-hydroxy-phenyl)-acrylic acid and 15.2 g of TBDMS-Cl in 10 ml of DMF was added 11.9 g of imidazole and the mixture was stirred at room temperature for 24 h. After aqueous work-up, the bis-silylated product was saponified with 2.1 g of LiOH in THF-H2O for 0.5 h at 0° C. The mixture was concentrated in vacuo and TBDMS-OH removed by extraction with hexane. The aqueous layer was acidified to pH 4 with KHSO4 and extracted with EtOAc. The organic phases were washed with brine, dried (Na2SO4) and evaporated to dryness. The semi-solid residue was suspended in hexane, filtered and the filtrate evaporated to dryness to yield 7.5 g of a pale yellow oil, which solidified upon standing.

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo and TBDMS-OH
  2. customremoved by extraction with hexane
  3. extractionextracted with EtOAc
  4. washThe organic phases were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated to dryness
  7. filtrationfiltered
  8. customthe filtrate evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-66880a3a91f5458492c6643a8c152417
Quelldatensatz
uspto-grants-2011_12
Patentnummer
USRE043006E1

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