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Sodium Carbonate → 4-{3-[6-(3-Benzo[1,3]dioxol-5-yl-5-thiophen-3-yl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester

HRID 420367
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 420367
[CH2:1]([O:3][C:4](=[O:41])[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]([C:28]3[CH:32]=[CH:31][S:30][CH:29]=3)[CH:25]=[C:24](I)[CH:23]=2)[C:10]=1[CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH3:2].[O:42]1[C:46]2[CH:47]=[CH:48][C:49](B(O)O)=[CH:50][C:45]=2[O:44][CH2:43]1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C(O)C.O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:3][C:4](=[O:41])[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]([C:28]3[CH:32]=[CH:31][S:30][CH:29]=3)[CH:25]=[C:24]([C:49]3[CH:48]=[CH:47][C:46]4[O:42][CH2:43][O:44][C:45]=4[CH:50]=3)[CH:23]=2)[C:10]=1[CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 3

HCID 10340Sodium CarbonateHCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 575865384-{3-[6-(3-Iodo-5-thiophen-3-yl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester

Produkt 1

HCID 575865534-{3-[6-(3-Benzo[1,3]dioxol-5-yl-5-thiophen-3-yl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl esterAusbeute 53,5 %

Reagenzien, Katalysatoren, Lösungsmittel

5
HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 4-{3-[6-(3-iodo-5-thiophen-3-yl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester (2.13 g, 3.06 mmol) in dimethoxyethane (75 mL) was stirred for 5 minutes at room temperature under nitrogen atmosphere. Then, tetrakis(triphenylphosphine)palladium(0) (1.06 g, 0.92 mmol) was added at room temperature and the resulting light yellow solution was heated to 80° C. and stirred for 5 minutes. At this period, a solution of benzo[1,3]dioxol-5-yl-boronic acid (1.53 g, 9.2 mmol) in ethanol (75 mL) was added followed by a solution of sodium carbonate (975 mg, 9.2 mmol) in water (6.0 mL). The resulting light yellow suspension was stirred for 24 h at reflux. Then, the reaction mixture was cooled to room temperature and diluted with water (100 mL) and ethyl acetate (100 mL). The two layers were separated and the aqueous layer was extracted with ethyl acetate (2×100 mL) and the combined organic extracts were washed with water (300 mL) and brine solution (300 mL). The organic layer was dried over anhydrous magnesium sulfate and filtration of the drying agent and removal of the solvent in vacuo gave the colored residue which was purified by using an ISCO 120 column, eluting with 0-20% ethyl acetate in hexanes to afford 4-{3-[6-(3-benzo[1,3]dioxol-5-yl-5-thiophen-3-yl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester (1.125 g, 53.5%) as a light brown viscous oil: ES(+)-HRMS m/e calculated for C40H46O8S (M+Na)+ 709.2805, found 709.2808.

Aufarbeitung

  1. waitAt this period
  2. stirringThe resulting light yellow suspension was stirred for 24 h
  3. temperatureat reflux
  4. temperatureThen, the reaction mixture was cooled to room temperature
  5. customThe two layers were separated
  6. extractionthe aqueous layer was extracted with ethyl acetate (2×100 mL)
  7. washthe combined organic extracts were washed with water (300 mL) and brine solution (300 mL)
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate and filtration of the drying agent and removal of the solvent in vacuo
  9. customgave the colored residue which
  10. customwas purified
  11. washeluting with 0-20% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-4be247d3a303480ca5ee686de206126c
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08093385B2

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