tert-Butyl acrylate → Methyl 1-(4-(3-(tert-butoxy)-3-oxopropoxy)phenyl)cyclopropane-1-carboxylate

HRID 503285Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 503285
[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:7][CH2:6]1)=[O:4].[C:15]([O:19][C:20](=[O:23])[CH:21]=[CH2:22])([CH3:18])([CH3:17])[CH3:16]>>[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH2:22][CH2:21][C:20]([O:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:23])=[CH:12][CH:13]=2)[CH2:6][CH2:7]1)=[O:4]

Komponenten

3

Edukt 2

HCID 15458tert-Butyl acrylateHCID 20770793Methyl 1-(4-hydroxyphenyl)cyclopropane-1-carboxylate

Produkt 1

HCID 59129236Methyl 1-(4-(3-(tert-butoxy)-3-oxopropoxy)phenyl)cyclopropane-1-carboxylateAusbeute 54 %

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of 1-(4-hydroxy-phenyl)-cyclopropanecarboxylic methyl ester (7.0 g, 3.6 mmol) in acrylic tert-butyl ester (50 mL) was added Na (42 mg, 1.8 mmol) at room temperature. The mixture was heated at 110° C. for 1 h. After cooling to room temperature, the resulting mixture was quenched with water and extracted with EtOAc (100 mL×3). The combined organic extracts were dried over anhydrous Na2SO4 and evaporated under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 20:1) to give 1-[4-(2-tert-butoxycarbonyl-ethoxy)-phenyl]-cyclopropanecarboxylic methyl ester (6.3 g, 54%) and unreacted start material (3.0 g). 1H NMR (300 MHz, CDCl3) δ 7.24 (d, J=8.7 Hz, 2H), 6.84 (d, J=8.7 Hz, 2H), 4.20 (t, J=6.6 Hz, 2H), 3.62 (s, 3H), 2.69 (t, J=6.6 Hz, 2H), 1.59-1.56 (m, 2H), 1.47 (s, 9H), 1.17-1.42 (m, 2H).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customthe resulting mixture was quenched with water
  3. extractionextracted with EtOAc (100 mL×3)
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. customevaporated under vacuum
  6. customto give the crude product, which
  7. customwas purified by column chromatography on silica gel (petroleum ether/ethyl acetate 20:1)

Quellen und Nachweise

ORD-Eintrag
ord-4ec933c373244fd9925abf43e76bb866
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776905B2

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