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Hydrochloric Acid → Methyl (3-(2-methanesulfonyloxyethyl)benzofuran-7-yloxy)acetate

HRID 430750
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 430750
[OH:1][CH2:2][CH2:3][C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:7]=2[O:6][CH:5]=1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28].Cl>ClCCl>[CH3:26][S:27]([O:1][CH2:2][CH2:3][C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:7]=2[O:6][CH:5]=1)(=[O:29])=[O:28]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11230436Methyl (3-(2-hydroxyethyl)benzofuran-7-yloxy)acetate

Produkt 1

HCID 11738940Methyl (3-(2-methanesulfonyloxyethyl)benzofuran-7-yloxy)acetateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Methyl (3-(2-hydroxyethyl)benzofuran-7-yloxy)acetate (4.12 g) was dissolved in dichloromethane (120 ml) and triethylamine (3 ml) and methanesulfonyl chloride (1.35 ml) were added to the solution, followed by stirring the resulting solution at 0° C. for 1.5 hours. The reaction mixture was then poured into 1N hydrochloric acid and the resultant was extracted with dichloromethane. The organic layer was washed with water, saturated aqueous sodium hydrogen carbonate solution, water, and with saturated saline, and dried over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure. The residue was recrystallized from n-hexane/ethyl acetate to obtain the desired compound (5.25 g, yield: 97%).

Aufarbeitung

  1. extractionthe resultant was extracted with dichloromethane
  2. washThe organic layer was washed with water, saturated aqueous sodium hydrogen carbonate solution, water
  3. dry with materialwith saturated saline, and dried over sodium sulfate
  4. customAfter removing the sodium sulfate
  5. filtrationby filtration
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was recrystallized from n-hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-548fb694717a44c78fb4457cbc5ff0c7
Quelldatensatz
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06323235B1

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