[3-(Tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-(3,5-dimethoxyphenyl)-methanol → [3-(Tert-butyldimethylsilanyloxy)-4-methoxyphenyl]-(3,5-dimethoxyphenyl)methanone

HRID 2378253Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2378253
[C:1]([Si:5]([CH3:28])([CH3:27])[O:6][C:7]1[CH:8]=[C:9]([CH:15]([C:17]2[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[C:19]([O:25][CH3:26])[CH:18]=2)[OH:16])[CH:10]=[CH:11][C:12]=1[O:13][CH3:14])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[C:1]([Si:5]([CH3:28])([CH3:27])[O:6][C:7]1[CH:8]=[C:9]([C:15]([C:17]2[CH:18]=[C:19]([O:25][CH3:26])[CH:20]=[C:21]([O:23][CH3:24])[CH:22]=2)=[O:16])[CH:10]=[CH:11][C:12]=1[O:13][CH3:14])([CH3:3])([CH3:2])[CH3:4]

Komponenten

4

Edukt 1

HCID 69204033[3-(Tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-(3,5-dimethoxyphenyl)-methanol

Produkt 1

HCID 69204700[3-(Tert-butyldimethylsilanyloxy)-4-methoxyphenyl]-(3,5-dimethoxyphenyl)methanoneAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysator2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of [3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-(3,5-dimethoxy-phenyl)-methanol (13.1 g, 32.4 mmol) in CH2Cl2 (330 mL) was added manganese dioxide (13.0 g, 150.0 mmol), and the mixture was stirred at ambient temperature for 8 h. Manganese dioxide (13.0 g, 150.0 mmol) was again added, and stirring proceeded for an additional 16 h. The mixture was filtered through Celite, and the sicciate was washed with CH2Cl2 (50 mL). The filtrate was evaporated, providing [3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-(3,5-dimethoxy-phenyl)-methanone as an oil (12.9 g, 99% yield): 1H NMR (CDCl3) δ 0.18 (s, 6H, 2SiCH3), 1.00 (s, 9H, SiC(CH3)3), 3.83 (s, 6H, 2OCH3), 3.89 (s, 3H, OCH3), 6.65 (t, J=2.4 Hz, 1H, Ar), 6.86-6.90 (m, 3H, Ar), 7.39-7.47 (m, 2H, Ar).

Aufarbeitung

  1. stirringstirring
  2. waitproceeded for an additional 16 h
  3. filtrationThe mixture was filtered through Celite
  4. washthe sicciate was washed with CH2Cl2 (50 mL)
  5. customThe filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-4e5bc64bddcc46d7bbbc194f184f5c53
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07470723B2

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