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Hydrochloric Acid → 2,3-Dihydro-1,4-benzodithiin-6-carbaldehyde

HRID 2193108
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2193108
Br[C:2]1[CH:11]=[CH:10][C:5]2[S:6][CH2:7][CH2:8][S:9][C:4]=2[CH:3]=1.C([Li])CCC.CCCCCC.[CH:23](OCC)=[O:24].Cl>C(OCC)(=O)C.O1CCCC1>[S:6]1[C:5]2[CH:10]=[CH:11][C:2]([CH:23]=[O:24])=[CH:3][C:4]=2[S:9][CH2:8][CH2:7]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 149644866-Bromo-2,3-dihydro-1,4-benzodithiinHCID 178418244HCID 178418244, Verbindung

Produkt 1

HCID 593980832,3-Dihydro-1,4-benzodithiin-6-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028
Tetrahydrofuran
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 5 mL of a tetrahydrofuran solution containing 500 mg of 6-bromo-2,3-dihydro-1,4-benzodithiin, 0.67 mL of a 2.67 mol/L butyllithium/hexane was added at −78° C., the mixture was stirred for 0.5 hour, then 300 mg of ethyl formate was added thereto, and the mixture was further stirred for 2 hours. Thereto was added 1 mol/L hydrochloric acid, and ethyl acetate was then added to the mixture. The organic layer was separated, washed with an aqueous saturated sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [silica gel; Silica gel 60N manufactured by Kanto Chemical Co., Inc., eluent; ethyl acetate:hexane 1:4] to obtain 121 mg of a brown oily substance, 2,3-dihydro-1,4-benzodithiin-6-carbaldehyde.

Aufarbeitung

  1. additionwas added at −78° C.
  2. stirringthe mixture was further stirred for 2 hours
  3. additionwas then added to the mixture
  4. customThe organic layer was separated
  5. washwashed with an aqueous saturated sodium hydrogen carbonate solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by silica gel column chromatography [silica gel; Silica gel 60N manufactured by Kanto Chemical Co., Inc., eluent; ethyl acetate:hexane 1:4]

Quellen und Nachweise

ORD-Eintrag
ord-5cbaf46ad22a48cfa9423265367ab23d
Quelldatensatz
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08329694B2

Notizen zur Reaktion

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