1-Bromo-3,5-dimethyladamantane → HCID 22633608, Verbindung

HRID 365632

Reaktionsgleichung

Reaktionsgleichung von HRID 365632
[CH3:1][C:2]12[CH2:12][CH:6]3[CH2:7][C:8]([CH3:11])([CH2:10][C:4](Br)([CH2:5]3)[CH2:3]1)[CH2:9]2.[C:14]([O-:17])(=[O:16])[CH3:15].[K+]>C(O)(=O)C>[C:14]([O:17][C:4]12[CH2:3][C:2]3([CH3:1])[CH2:12][CH:6]([CH2:7][C:8]([CH3:11])([CH2:9]3)[CH2:10]1)[CH2:5]2)(=[O:16])[CH3:15]

Komponenten

4

Edukt 2

HCID 983171-Bromo-3,5-dimethyladamantaneHCID 517044Potassium Acetate

Produkt 1

HCID 22633608HCID 22633608, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

2.486 (10.2 mmoles) of 3,5-dimethyl-1-bromoadamantane is refluxed for 16 hours with 2.034 g (20.7 mmoles) of potassium acetate in 10 mL of acetic acid. The solution is poured over 100 grams of ice, allowed to melt, and extracted with 3×10 mL of diethyl ether. The combined ether extracts are washed with saturated aqueous sodium bicarbonate followed by saturated aqueous sodium chloride, then dried over sodium sulfate. The solvent is removed under vacuum, yielding 1.521 (67%) of the desired product, a colorless oil. TLC: Rf=0.68 (silica plate: eluant hexane 90%, ethyl acetate 10%). 1HNMR (CDCl3, 500 Mhz): 0.858 (s, 6H), 1.115 (d, 2H, J=12.4 Hz), 1.177 (d, 2H, J=12.4 Hz), 1.260 (d, 2H, J=12.3 Hz), 1.367 (d, 2H, J=12.3 Hz), 1.714 (d, 2H, J=11.6 Hz), 1.766 (d, 2H, J=11.6 Hz), 1.939 (s, 2H), 1.976 (s, 3H), 2.191 (m, 1H).

Aufarbeitung

  1. extractionextracted with 3×10 mL of diethyl ether
  2. washThe combined ether extracts are washed with saturated aqueous sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-199c474a196e4bd9839f8c11963e69b3
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06127415

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