Water → methyl (Z)-4-benzyloxy-3-(1-methyl-propenyl)-benzoate

HRID 1406703Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1406703
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:26]/[C:27](/B(O)O)=[CH:28]/[CH3:29].O>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1/[C:27](/[CH3:26])=[CH:28]\[CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 11389361(E)-But-2-EN-2-ylboronic acidHCID 23111814Methyl 4-(benzyloxy)-3-bromobenzoate

Produkt 1

HCID 57830180methyl (Z)-4-benzyloxy-3-(1-methyl-propenyl)-benzoateAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl 4-benzyloxy-3-bromobenzoate (1.61 g, 5.0 mmol), caesium carbonate (4.89 g, 15.0 mmol), (E)-2-buten-2-yl boronic acid (600 mg, 6.0 mmol) and [1,1′-bis(diphenylphosphino)ferrocenyl]palladium (II) chloride (204 mg, 0.25 mmol) were dissolved in anhydrous tetrahydrofuran (100 ml), water (10 ml) was added and the mixture was stirred and held at reflux under an atmosphere of nitrogen for 16 hours. Upon cooling the solvent was removed in vacuo and the mixture partitioned between dichloromethane and water. The organic layer was separated, the solvent removed in vacuo and the residue subjected to column chromatography on silica. Elution with 5% ethyl acetate in petroleum ether afforded methyl (Z)-4-benzyloxy-3-(1-methyl-propenyl)-benzoate (600 mg, 41%) as a colourless solid. 1H NMR (DMSO-d6) 7.88 (1H, dd), 7.59 (1H, d), 7.40 (4H, m), 7.34 (1H, m), 7.23 (1H, d), 5.57 (1H, q), 5.21 (2H, s), 3.82 (3H, s), 1.94 (3H, s), 1.38 (3H, d).

Aufarbeitung

  1. temperatureat reflux under an atmosphere of nitrogen for 16 hours
  2. temperatureUpon cooling the solvent
  3. customwas removed in vacuo
  4. customthe mixture partitioned between dichloromethane and water
  5. customThe organic layer was separated
  6. customthe solvent removed in vacuo
  7. washElution with 5% ethyl acetate in petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-1ec4c9c143f94fe7aacb627be01d369f
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08916552B2

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