tert-Butyl acrylate → tert-Butyl 3-[2-(4-bromophenyl)ethoxy]propanoate

HRID 2234182Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2234182
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1.[C:23]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])(=[O:26])[CH:24]=[CH2:25]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][CH2:25][CH2:24][C:23]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 15458tert-Butyl acrylateHCID 66854Benzyltrimethylammonium hydroxideHCID 728512-(4-Bromophenyl)ethanol

Produkt 1

HCID 69136052tert-Butyl 3-[2-(4-bromophenyl)ethoxy]propanoateAusbeute 66,2 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-(4-Bromophenyl)ethanol (5 g) was treated with benzyltrimethylammonium hydroxide (Triton B®) (0.3 mL) and the resultant mixture was stirred in vacuo for 30 minutes. The mixture was then cooled to 0° C. and treated with t-butyl acrylate (3.5 g). The reaction was warmed to room temperature and stirred for 5 hours. The mixture was filtered through aluminium oxide (15 g) eluting with ether (75 mL). The collected filtrate was concentrated and purified by flash chromatography eluting with ethylacetate:iso-hexane (1:8) to give the sub-titled compound (5.42 g) as an oil.

Aufarbeitung

  1. temperatureThe reaction was warmed to room temperature
  2. filtrationThe mixture was filtered through aluminium oxide (15 g)
  3. washeluting with ether (75 mL)
  4. concentrationThe collected filtrate was concentrated
  5. custompurified by flash chromatography
  6. washeluting with ethylacetate:iso-hexane (1:8)

Quellen und Nachweise

ORD-Eintrag
ord-439c951efb204572a5b85acff77ebe64
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709511B2

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