Sodium hydride → 2-(4-(2-Methoxyethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 57521

Reaktionsgleichung

Reaktionsgleichung von HRID 57521
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[O:3]1.[H-].[Na+].[CH3:19][O:20][CH2:21][CH2:22]Br>CN(C=O)C>[CH3:19][O:20][CH2:21][CH2:22][O:15][C:12]1[CH:13]=[CH:14][C:9]([B:4]2[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]2)=[CH:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Produkt 1

HCID 684654432-(4-(2-Methoxyethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneAusbeute 60,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (150 mg, 0.682 mmol) in DMF (5 mL) was added 60% NaH (136 mg, 3.41 mmol) and 2-bromoethyl methyl ether (0.13 mL, 1.363 mmol). The resulting solution was stirred at 50° C. overnight, cooled to ambient temperature, quenched with water, and extracted with EtOAc. The combined extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography to give the title compound (114 mg, 60% yield).

Aufarbeitung

  1. temperaturecooled to ambient temperature
  2. customquenched with water
  3. extractionextracted with EtOAc
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-54b3315cffc04387a3fc58752d298f1b
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434726B2

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