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Trifluoroacetic acid → alpha-(RS)-allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-methylamine trifluoroacetate

HRID 850873
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 850873
C[Si]([N-:5][Si](C)(C)C)(C)C.[Li+].Cl[CH:12]([B:16]1[O:20][C:19]([CH3:22])([CH3:21])[C:18]([CH3:24])([CH3:23])[O:17]1)[CH2:13][CH:14]=[CH2:15].[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28]>O1CCCC1>[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28].[CH2:13]([CH:12]([B:16]1[O:20][C:19]([CH3:22])([CH3:21])[C:18]([CH3:24])([CH3:23])[O:17]1)[NH2:5])[CH:14]=[CH2:15]
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Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 2733832Lithium hexamethyldisilazaneHCID 126805082-(1-Chlorobut-3-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Produkt 1

HCID 19364663alpha-(RS)-allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-methylamine trifluoroacetateAusbeute 24,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

6.6 ml (6.6 mmol) of 1M lithium bis(trimethylsilyl)amide in tetrahydrofuran were added dropwise to a solution of 1.43 g (6.6 mmol) of 2-(1 (RS)-chloro-3-butenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in 20 ml of tetrahydrofuran under nitrogen at -78° C. The solution was then stirred overnight at room temperature. The solvent was removed by evaporation and the residue was taken up in diethyl ether. Insoluble material was removed by filtration and the filtrate was cooled to 0° C. 1.5 ml (19.8 mmol) of trifluoroacetic acid were added and the solution was stirred at 0° C. for 30 minutes. The resulting precipitate was filtered off and dried to give 0.5 g of α-(RS)-allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-methylamine trifluoroacetate which was used in the next step without further purification.

Aufarbeitung

  1. customThe solvent was removed by evaporation
  2. customInsoluble material was removed by filtration
  3. temperaturethe filtrate was cooled to 0° C
  4. stirringthe solution was stirred at 0° C. for 30 minutes
  5. filtrationThe resulting precipitate was filtered off
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e7aff404efea4701ab6f8ef2931a5863
Quelldatensatz
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06018020

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