Water → 2-(3,6-dihydro-2H-pyran-4-yl)-4,6-dimethylphenol

HRID 63385

Reaktionsgleichung

Reaktionsgleichung von HRID 63385
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[O:11]1[CH2:16][CH:15]=[C:14](B2OC(C)(C)C(C)(C)O2)[CH2:13][CH2:12]1.C(=O)([O-])[O-].[Na+].[Na+].O>C(COC)OC>[O:11]1[CH2:12][CH:13]=[C:14]([C:2]2[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=2[OH:10])[CH2:15][CH2:16]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2999762-Bromo-4,6-dimethylphenolHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol ester

Produkt 1

HCID 900035562-(3,6-dihydro-2H-pyran-4-yl)-4,6-dimethylphenolAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

2-Bromo-4,6-dimethylphenol (430 mg, 2.14 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (494 mg, 2.35 mmol), Pd(dbpf)Cl2 (69.7 mg, 0.11 mmol) and sodium carbonate (680 mg, 6.45 mmol) were dissolved in dimethoxyethane:water=3 mL:1 mL, followed by stirring in microwave at 120° C. for 30 minutes. The reaction mixture was filtered through Celite. The filtrate was concentrated under reduced pressure, and purified by column chromatography (silica gel; hexane/ethyl acetate, 9/1) to obtain 2-(3,6-dihydro-2H-pyran-4-yl)-4,6-dimethylphenol (160 mg, 37%) as a colorless oil.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. custompurified by column chromatography (silica gel; hexane/ethyl acetate, 9/1)

Quellen und Nachweise

ORD-Eintrag
ord-18d91e762c364dd286800cb2f4e0cfe4
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447083B2

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