Ethyl Bromide → 2-[2-(2,5-Dimethylphenoxymethyl)-alpha-hydroxybenzyl]pyridine

HRID 369117Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 369117
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=1[CH3:17].[Mg].Br[CH2:20][CH3:21].[Cl-].[NH4+:23].[CH2:24]1[CH2:28][O:27][CH2:26][CH2:25]1>>[CH3:17][C:11]1[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:10]=1[O:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH:26]([C:25]1[CH:24]=[CH:28][CH:21]=[CH:20][N:23]=1)[OH:27]

Komponenten

6

Edukt 5

HCID 6332Ethyl BromideHCID 8028Tetrahydrofuran3×HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 109462162-Bromobenzyl-(2,5-dimethylphenyl)ether

Produkt 1

HCID 155451342-[2-(2,5-Dimethylphenoxymethyl)-alpha-hydroxybenzyl]pyridineAusbeute 75,8 %

Reaktionsbedingungen

Temperatur
52.5 °C

Versuchsvorschrift

A mixture of 2.91 g (0.01 mol) of 1-bromo-2-(2,5-dimethylphenoxymethyl) benzene and 8 ml of THF was added to a suspension of 0.36 g (0.015 mol) of magnesium, 0.1 ml of bromoethane, and 2 ml of tetrahydrofuran at 45 to 55° C. over 5 minutes under a nitrogen gas atmosphere and stirred at 50 to 55° C. for an hour to prepare a Grignard's reagent. The Grignard's reagent was added to a mixture of 1.18 g (0.011 mol) of 2-pyridinecarboxyaldehyde and 10 ml of THF below 5° C. over 15 minutes and stirred at room temperature for 2 hours. After completion of the reaction, 150 ml of an aqueous solution of ammonium chloride was added and extracted with 150 ml of ether. After the extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, the residue thus obtained was purified by column chromatography on silica gel (ethyl acetate/n-hexane) to give 2.42 g of 2-[2-(2,5-dimethylphenoxymethyl)-α-hydroxybenzyl]pyridine (75.8% yield) as colorless oil.

Aufarbeitung

  1. customto prepare a Grignard's reagent
  2. stirringstirred at room temperature for 2 hours
  3. additionwas added
  4. extractionextracted with 150 ml of ether
  5. dry with materialAfter the extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe residue thus obtained
  8. customwas purified by column chromatography on silica gel (ethyl acetate/n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-148acbfe0578434bbbea04fe0df4d251
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06136837

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