Ethyl Acetate → 2-(4-(2-Methoxyethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 2194584

Reaktionsgleichung

Reaktionsgleichung von HRID 2194584
[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.Br[CH2:18][CH2:19][O:20][CH3:21].C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[CH3:21][O:20][CH2:19][CH2:18][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

6

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 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 25,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (1 g, 4.5 mmole), 1-bromo-2-methoxyethane (0.7 g, 5 mmole) and K2CO3 (1.3 g, 9 mmole) in DMF (10 mL) was heated at 85° C. for 20 hr, diluted by ethyl acetate, washed by water, dried over MgSO4, filtered, concentrated under vacuum, purified by ISCO (silica gel, elute: 10% ethyl acetate in hexane) to give liquid product (316 mg, 25% yield). MS (ESI) m/z: Calc. 278.2 (M+). Found: 279.3 (M++1).

Aufarbeitung

  1. washwashed by water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. custompurified by ISCO (silica gel, elute: 10% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-4daaae064e594dfd8ec53aa3a35292b2
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08334292B1

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