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Water → HCID 70818258, Verbindung

HRID 591055
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 591055
C(=O)([O-])[O-].[Na+].[Na+].O.I[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:15]([O:19][CH:20]([C:26]1[C:30](B2OC(C)(C)C(C)(C)O2)=[C:29]([CH3:40])[S:28][C:27]=1[CH3:41])[C:21]([O:23][CH2:24][CH3:25])=[O:22])([CH3:18])([CH3:17])[CH3:16]>CN(C)C=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[C:15]([O:19][CH:20]([C:26]1[C:30]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:29]([CH3:40])[S:28][C:27]=1[CH3:41])[C:21]([O:23][CH2:24][CH3:25])=[O:22])([CH3:18])([CH3:17])[CH3:16]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962Water2×HCID 10340Sodium CarbonateHCID 11575IodobenzeneHCID 70818507HCID 70818507, Verbindung

Produkt 1

HCID 70818258HCID 70818258, VerbindungAusbeute 75,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Katalysator
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Under argon atmosphere, sodium carbonate (18 mg, 0.169 mmol), water (1.1 mL) and iodobenzene (19 μL, 0.17 mmol) were added to a solution of ethyl 2-(tert-butoxy)-2-[2,5-dimethyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-3-yl]acetate (28f) (70 mg, 0.16 mmol) in N,N-dimethylformamide (3.4 mL). The solution was degassed under argon and palladium tetrakis(triphenylphosphine) (37 mg, 0.032 mmol) was added. The mixture was heated at 100° C. for 3 hours. The mixture was then cooled at room temperature, water was added and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by preparative TLC (cyclohexane/ethyl acetate 90/10) to afford the desired product ethyl (28g) (42 mg, 0.121 mmol, 75%).

Aufarbeitung

  1. customThe solution was degassed under argon
  2. temperatureThe mixture was then cooled at room temperature
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by preparative TLC (cyclohexane/ethyl acetate 90/10)

Quellen und Nachweise

ORD-Eintrag
ord-b0fb9884d5d946d3aa859016ef81b95e
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09238026B2

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