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2-(Dichloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 2-[1(RS)-chlorobutyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 850877
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 850877
[Cl:1][CH:2](Cl)[B:3]1[O:7][C:6]([CH3:9])([CH3:8])[C:5]([CH3:11])([CH3:10])[O:4]1.[CH2:13]([Mg]Br)[CH2:14][CH3:15]>O1CCCC1>[Cl:1][CH:2]([B:3]1[O:7][C:6]([CH3:9])([CH3:8])[C:5]([CH3:11])([CH3:10])[O:4]1)[CH2:13][CH2:14][CH3:15]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 110420412-(Dichloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178455851HCID 178455851, Verbindung

Produkt 1

HCID 193646772-[1(RS)-chlorobutyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneAusbeute 73,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

0.5 g (2.37 mmol) of 2-(dichloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was dissolved in 10 ml of tetra-hydrofuran and the solution was cooled under a nitrogen atmosphere to -78° C. 2.4 ml (2.4 mmol) of 1M propylmagnesium bromide were added dropwise and the solution was stirred at room temperature for 18 hours. The solution was partitioned between ethyl acetate, saturated sodium chloride solution and 2M hydrochloric acid solution. The aqueous layer was extracted with ethyl acetate and the organic layers were combined and dried over anhydrous sodium sulphate. After evaporation there was obtained 0.38 g of 2-[1(RS)-chlorobutyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane as an oil which was used in the next step without further purification.

Aufarbeitung

  1. customThe solution was partitioned between ethyl acetate, saturated sodium chloride solution and 2M hydrochloric acid solution
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialdried over anhydrous sodium sulphate
  4. customAfter evaporation

Quellen und Nachweise

ORD-Eintrag
ord-a6d4ffc18dba4ee381b3d757179a9a04
Quelldatensatz
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06018020

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