Imidazole → 6-(Tert-butyl-diphenyl-silanyloxy)-benzofuran-3-one

HRID 222464Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 222464
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[CH:3]=1.N1C=CN=C1.[C:17]([Si:21]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)Cl)([CH3:20])([CH3:19])[CH3:18]>ClCCl.[Cl-].[Na+].O>[C:17]([Si:21]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[O:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[CH:3]=1)([CH3:20])([CH3:18])[CH3:19]

Komponenten

6

Edukt 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 2357176-Hydroxy-3-coumaranone

Produkt 1

HCID 685261616-(Tert-butyl-diphenyl-silanyloxy)-benzofuran-3-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of 6-hydroxy-benzofuran-3-one (1.01 g, 6.73 mmol) in dry dichloromethane (18 mL) was added imidazole (0.458 g, 6.727 mmol) followed by tert-butyldiphenylchlorosilane (1.72 mL, 6.73 mmol) at room temperature. The mixture was stirred overnight and poured into brine. The aqueous phase was extracted with dichloromethane. The combined organic layers were dried over Na2SO4, evaporated in vacuo and the residue was purified by column chromatography (ethylacetate:hexane; 1:9) to give the 6-(tert-butyl-diphenyl-silanyloxy)-benzofuran-3-one as slightly yellow oil (1.34 g, 52%). 1H NMR (CDCl3, 400 MHz) 1.21 (s, 9H), 4.54 (s, 2H), 6.40 (s, 1H), 6.55 (dd, J=1.6, 8.0 Hz, 1H), 7.38-7.50 (m, 7H), 7.67 (m, 4H).

Aufarbeitung

  1. extractionThe aqueous phase was extracted with dichloromethane
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customevaporated in vacuo
  4. customthe residue was purified by column chromatography (ethylacetate:hexane; 1:9)

Quellen und Nachweise

ORD-Eintrag
ord-6079800153794aac983a1ae9d9c44a76
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207216B2

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