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Ethyl formate → HCID 18319635, Verbindung

HRID 1699373
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1699373
[O-]CC.[Na+].I[C:6]1[C:16]2[O:15][CH2:14][CH2:13][C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.[CH:22]([O:24][CH2:25][CH3:26])=[O:23]>ClCCl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:25]([O:24][C:22]([C:6]1[C:16]2[O:15][CH2:14][CH2:13][C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1)=[O:23])[CH3:26]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8025Ethyl formateHCID 2723922Sodium ethoxideHCID 18319552HCID 18319552, Verbindung

Produkt 1

HCID 18319635HCID 18319635, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysator
HCID 6344
Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a mixture of sodium ethoxide (1.7 ml, 20% in ethanol) and dichlorobis(triphenylphosphine)palladium(II) (14 mg) in dichloromethane (7 ml) was added a mixture of ethyl 2,3-dihydro-9-iodo-1-benzoxepin-4-carboxylate (0.69 g) and ethyl formate (0.28 ml) at ambient temperature under nitrogen atmosphere. The reaction mixture was stirred at 40° C. for 3 hours and filtered off. The filtrate was partitioned between diethyl ether and 1N hydrochloric acid. The organic layer was washed successively with saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was purified by medium pressure liquid chromatography (silica gel) using a mixture of ethyl acetate and n-hexane (1:19) as an eluent to give a solid of ethyl 2,3-dihydro-9-ethoxycarbonyl-1-benzoxepin-4-carboxylate (120 mg).

Aufarbeitung

  1. additionwas added
  2. filtrationfiltered off
  3. customThe filtrate was partitioned between diethyl ether and 1N hydrochloric acid
  4. washThe organic layer was washed successively with saturated aqueous sodium bicarbonate and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by medium pressure liquid chromatography (silica gel)
  8. additiona mixture of ethyl acetate and n-hexane (1:19) as an eluent

Quellen und Nachweise

ORD-Eintrag
ord-c0705d79d988482492ae2f6ed8dc4030
Quelldatensatz
uspto-grants-2002_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06346527B1

Notizen zur Reaktion

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