Triethylamine → 2-Bromo-2-methyl-propionic acid 2-(2,2-dimethoxy-ethoxy)-ethyl ester

HRID 80297

Reaktionsgleichung

Reaktionsgleichung von HRID 80297
[CH3:1][O:2][CH:3]([O:9][CH3:10])[CH2:4][O:5][CH2:6][CH2:7][OH:8].C(N(CC)CC)C.[Br:18][C:19]([CH3:24])([CH3:23])[C:20](Br)=[O:21]>C(Cl)Cl>[CH3:1][O:2][CH:3]([O:9][CH3:10])[CH2:4][O:5][CH2:6][CH2:7][O:8][C:20](=[O:21])[C:19]([Br:18])([CH3:24])[CH3:23]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 886852-Bromo-2-methylpropionyl bromideHCID 197362752-(2,2-Dimethoxyethoxy)ethan-1-ol

Produkt 1

HCID 593915972-Bromo-2-methyl-propionic acid 2-(2,2-dimethoxy-ethoxy)-ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 2-(2,2-dimethoxy-ethoxy)-ethanol (2.20 g, 14.6 mmol) from Example 9 in dry triethylamine (3.0 mL, 21 mmol) and dry methylene chloride (30 mL) was stirred at 0° C. 2-bromo-2-methylpropionyl bromide (1.7 mL, 14 mmol) methylene chloride (10 mL) was then added to the alcohol over a 15 minute period. The reaction mixture was warmed to room temperature and stirred overnight. The reaction mixture was filtered, the filtrate was washed with saturated sodium bicarbonate, and dried with magnesium sulfate. The solvent was removed and the yellow oil purified by column chromatography. 1H NMR (300 MHz, CDCl3): δ=1.78 (s, 6H), 3.31 (s, 6H), 3.49 (d, 2H), 3.68 (t, 2H), 4.25 (t, 2H), 4.46 (t, 1H) 13C NMR (300 MHz, CDCl3): δ=31.23, 55.85, 56.15, 65.58, 69.55, 71.44, 103.09, 172.07.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. washthe filtrate was washed with saturated sodium bicarbonate
  3. dry with materialdried with magnesium sulfate
  4. customThe solvent was removed
  5. customthe yellow oil purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-16ef7506915c4bbc8e3d335a930919f5
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846021B2

Verknüpfte Notizen

Wird geladen…