2,6-Lutidine → (3-Fluoro-4-nitrobenzyloxy)triisopropylsilane

HRID 518597Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 518597
[F:1][C:2]1[CH:3]=[C:4]([CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].FC(F)(F)S(O[Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])(=O)=O.CC1C=CC=C(C)N=1>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])[CH2:11][O:12][Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21]

Komponenten

5

Edukt 3

HCID 79372,6-LutidineHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 27746583-Fluoro-4-nitrobenzyl alcohol

Produkt 1

HCID 60195384(3-Fluoro-4-nitrobenzyloxy)triisopropylsilaneAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a 3-L round-bottomed flask was added (3-fluoro-4-nitrophenyl)methanol (4.7 g, 27.5 mmol) and DCM (47 mL). To the mixture was added triisopropylsilyl trifluoromethanesulfonate (9.26 g, 30.2 mmol) and 2,6-dimethylpyridine (3.53 g, 33.0 mmol). The resulting mixture was stirred for 3 hours at RT, and washed with NH4Cl (5-250 mL) and H2O (5-250 mL). The organic layer was collected and dried over sodium sulfate and concentrated to afford (3-fluoro-4-nitrobenzyloxy)triisopropylsilane (8.9 g, 99% yield) as a light yellow oil.

Aufarbeitung

  1. washwashed with NH4Cl (5-250 mL) and H2O (5-250 mL)
  2. customThe organic layer was collected
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-78eca634cba14ca0a10bcf6f69fde987
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115127B2

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