Ethyl Acetate → HCID 57708911, Verbindung

HRID 546824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 546824
C1(C)C=CC(S([O:10][CH2:11][C@@H:12]2[O:16][C:15](=[O:17])[CH2:14][CH2:13]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].[CH2:25]([C:27]([C:46]1[CH:51]=[CH:50][C:49](O)=[C:48]([CH3:53])[CH:47]=1)([C:30]1[CH:35]=[CH:34][C:33]([B:36]2[O:40][C:39]([CH3:42])([CH3:41])[C:38]([CH3:44])([CH3:43])[O:37]2)=[C:32]([CH3:45])[CH:31]=1)[CH2:28][CH3:29])[CH3:26].C(OCC)(=O)C>CN(C)C=O>[CH2:25]([C:27]([C:46]1[CH:51]=[CH:50][C:49]([O:10][CH2:11][C@@H:12]2[O:16][C:15](=[O:17])[CH2:14][CH2:13]2)=[C:48]([CH3:53])[CH:47]=1)([C:30]1[CH:35]=[CH:34][C:33]([B:36]2[O:40][C:39]([CH3:41])([CH3:42])[C:38]([CH3:43])([CH3:44])[O:37]2)=[C:32]([CH3:45])[CH:31]=1)[CH2:28][CH3:29])[CH3:26]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 7021461[(2R)-5-Oxooxolan-2-yl]methyl 4-methylbenzene-1-sulfonateHCID 577091704-{1-Ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenol

Produkt 1

HCID 57708911HCID 57708911, VerbindungAusbeute 76,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

(R)-(−)-Dihydro-5-(p-tolyl-sulfonyloxymethyl)-2(3H)-furanone (293 mg, 1.084 mmol) and potassium carbonate (180 mg, 1.301 mmol) were added to a solution of 4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenol (Example 15-(2); 171 mg, 0.434 mmol) in N,N-dimethylformamide (1.5 mL) at room temperature, and the mixture was stirred at 110° C. for one hour. Ethyl acetate was added to the reaction solution. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate=80/20 to ethyl acetate only) to give the title compound (164 mg, 76.8%).

Aufarbeitung

  1. washThe organic layer was washed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel chromatography (n-hexane/ethyl acetate=80/20 to ethyl acetate only)

Quellen und Nachweise

ORD-Eintrag
ord-04747f29b74a491ea96a7c3a1cb6038c
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935688B2

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