Allyl bromide → Methyl 2-allyloxy-5-methoxybenzoate

HRID 1643542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1643542
C([O-])([O-])=O.[K+].[K+].[CH2:7](Br)[CH:8]=[CH2:9].[OH:11][C:12]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:13]=1[C:14]([O:16][CH3:17])=[O:15]>CN(C=O)C>[CH3:17][O:16][C:14](=[O:15])[C:13]1[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:12]=1[O:11][CH2:9][CH:8]=[CH2:7]

Komponenten

5

Edukt 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 4072341Methyl 2-hydroxy-5-methoxybenzoate

Produkt 1

HCID 59560455Methyl 2-allyloxy-5-methoxybenzoateAusbeute 82,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

K2CO3 (4.64 g, 33.6 mmol) and allyl bromide (1.56 mL, 18.5 mmol) were added to a solution of methyl 2-hydroxy-5-methoxybenzoate (2.5 mL, 16.8 mmol) in DMF (10 mL). The reaction mixture was heated to 60° C. for 1 h, and then quenched with H2O (80 mL) and extracted with EtOAc (2×80 mL). The organic layers were washed with H2O (150 mL), dried over MgSO4 and concentrated. The residue was purified by flash column chromatograph eluting with 5-10% EtOAc/hexane to give a colorless oil (3.07 g, 82%). 1H NMR (400 MHz, CDCl3) δ 7.34 (d, J=3.28 Hz, 1 H) 6.98-7.03 (m, 1H) 6.90-6.94 (m, 1 H) 6.01-6.11 (m, 1 H) 5.44-5.51 (m, 1 H) 5.25-5.31 (m, 1 H) 4.57 (td, J=3.28, 1.52 Hz, 2 H) 3.91 (s, 3 H) 3.80 (s, 3 H).

Aufarbeitung

  1. customquenched with H2O (80 mL)
  2. extractionextracted with EtOAc (2×80 mL)
  3. washThe organic layers were washed with H2O (150 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatograph
  7. washeluting with 5-10% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-bc709be029b4426c946ba915689a8a83
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08119624B2

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