Cesium carbonate → 2-(5-Benzyloxy-2-but-1-enylphenoxy)-2-methylpropionic Acid Ethyl Ester

HRID 1609973Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1609973
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:16]=[CH:17][CH2:18][CH3:19])=[C:13]([OH:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:21]([CH3:28])([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:25]([O:24][C:22](=[O:23])[C:21]([O:15][C:13]1[CH:14]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=[CH:11][C:12]=1[CH:16]=[CH:17][CH2:18][CH3:19])([CH3:28])[CH3:27])[CH3:26]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 693132605-Benzyloxy-2-but-1-enylphenol

Produkt 1

HCID 693103232-(5-Benzyloxy-2-but-1-enylphenoxy)-2-methylpropionic Acid Ethyl EsterAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

5-Benzyloxy-2-but-1-enylphenol (0.70 g, 2.75 mmol) was dissolved in anhydrous DMF (12 mL), followed by the addition of ethyl bromoisobutyrate (1.62 mL, 11.0 mmol), and cesium carbonate (3.58 g, 11.0 mmol). The mixture was then heated for 18 h (55° C.). The reaction mixture was then cooled and concentrated in vacuo. The crude residue was partitioned between EtOAc (70 mL) and water (40 mL). The organic layer was washed with brine, dried (Na2SO4), and removed in vacuo. The crude residue was purified using radial chromatography, eluting with 5% EtOAc/Hex to give 0.77 g (76%) of a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.41-7.28 (m, 6H), 6.65-6.59 (m, 2H), 6.40 (d, J=2.4 Hz, 1H), 6.14-6.07 (m, 1H), 4.99 (s, 2H), 4.22 (q, J=7.2 Hz, 2H), 2.22 (quintet, J=7.6 Hz, 2H), 1.56 (s, 6H), 1.26 (t, J=7.1 Hz, 3H), 1.08 (t, J=7.6 Hz, 3H), MS (ES) m/e 369 (M+1).

Aufarbeitung

  1. temperatureThe reaction mixture was then cooled
  2. concentrationconcentrated in vacuo
  3. customThe crude residue was partitioned between EtOAc (70 mL) and water (40 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customremoved in vacuo
  7. customThe crude residue was purified
  8. washeluting with 5% EtOAc/Hex

Quellen und Nachweise

ORD-Eintrag
ord-423e786a65ec48ccaff7245a10bdc06f
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06982278B2

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