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1,2-Dimethoxyethane → HCID 59496796, Verbindung

HRID 416986
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 416986
[CH2:1]([O:3][C:4](=[O:39])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([O:28][CH2:29][CH3:30])[CH:25]=[C:24](Br)[CH:23]=2)[C:10]=1[CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH3:2].[CH2:40]1[O:48][C:47]2[CH:46]=[CH:45][C:44](B(O)O)=[CH:43][C:42]=2[O:41]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(COC)OC>O.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:1]([O:3][C:4](=[O:39])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([O:28][CH2:29][CH3:30])[CH:25]=[C:24]([C:45]3[CH:44]=[CH:43][C:42]4[O:41][CH2:40][O:48][C:47]=4[CH:46]=3)[CH:23]=2)[C:10]=1[CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 59496797HCID 59496797, Verbindung

Produkt 1

HCID 59496796HCID 59496796, VerbindungAusbeute 99,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Katalysator
HCID 962WaterLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
96 °C

Versuchsvorschrift

To a mixture of 4-[3-[6-(3-bromo-5-ethoxy-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (155 mg, 0.255 mmol), 3,4-methylenedioxybenzeneboronic acid (85 mg, 0.51 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (73 mg, 0.1 mmol), and cesium carbonate (166 mg, 0.51 mmol) was added dimethoxyethane (10 mL) at room temperature under nitrogen atmosphere. The resulting brown reaction mixture was heated to 96° C. and stirred for 15 h at which time the TLC analysis of the reaction mixture indicated the absence of starting material. Then, the reaction mixture was cooled to room temperature and diluted with water (50 mL) and ethyl acetate (50 mL). The two layers were separated and the aqueous layer was extracted with ethyl acetate (50 mL) and the combined organic extracts were washed with water (50 mL) and brine solution (50 mL). The organic layer was dried over anhydrous magnesium sulfate and filtration of the drying agent and removal of the solvent under vacuum gave the colored residue which was purified by using an ISCO 40 column, eluting with 0-25% ethyl acetate in hexanes to obtain 4-[3-[6-(3-benzo[1,3]dioxol-5-yl-5-ethoxy-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (165 mg, 99%) as a colorless viscous oil: ES(+)-LRMS m/e calcd for C38H48O9 (M+Na)+ 671.3190. found 671.3185.

Aufarbeitung

  1. temperatureThen, the reaction mixture was cooled to room temperature
  2. customThe two layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (50 mL)
  4. washthe combined organic extracts were washed with water (50 mL) and brine solution (50 mL)
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate and filtration of the drying agent and removal of the solvent under vacuum
  6. customgave the colored residue which
  7. customwas purified
  8. washeluting with 0-25% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-e661bfeb2eab433ab513316bdff79087
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08088936B2

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