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Methanol → HCID 19782180, Verbindung

HRID 258021
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 258021
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([C:12]([O:14]CC)=[O:13])[CH2:6]2.B(Br)(Br)Br.CO>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([C:12]([OH:14])=[O:13])[CH2:6]2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 887MethanolHCID 25134Boron tribromideHCID 19782198HCID 19782198, Verbindung

Produkt 1

HCID 19782180HCID 19782180, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

50 g (0.23 mol) of the compound from Example 13 are initially introduced in 780 ml of absolute CH2Cl2 at -78° C. 114 ml (1.2 mol) of boron tribromide in 360 ml of absolute CH2Cl2 are then added dropwise and the mixture is stirred at -78° C. for 30 minutes. It is then stirred at 0° C. for 2.5 h, subsequently cooled to -78° C. again and 690 ml of absolute MeOH are added cautiously. After 15 minutes, the mixture is evaporated, the residue is dissolved in 818 ml of MeOH, 272 ml of 2N NaOH solution are added and the mixture is stirred at 20° C. for 2 h. The methanol is evaporated in vacuo, the aqueous phase is washed with 200 ml of ethyl acetate and then acidified to pH 1-2 using concentrated hydrochloric acid with ice cooling. The aqueous phase is shaken twice with 100 ml of ethyl acetate each time, and the combined ethyl acetate phases are dried over Na2SO4 and evaporated. The residue is recrystallized from toluene.

Aufarbeitung

  1. stirringIt is then stirred at 0° C. for 2.5 h
  2. temperaturesubsequently cooled to -78° C. again
  3. waitAfter 15 minutes
  4. customthe mixture is evaporated
  5. dissolutionthe residue is dissolved in 818 ml of MeOH
  6. addition272 ml of 2N NaOH solution are added
  7. stirringthe mixture is stirred at 20° C. for 2 h
  8. customThe methanol is evaporated in vacuo
  9. washthe aqueous phase is washed with 200 ml of ethyl acetate
  10. stirringThe aqueous phase is shaken twice with 100 ml of ethyl acetate each time
  11. dry with materialthe combined ethyl acetate phases are dried over Na2SO4
  12. customevaporated
  13. customThe residue is recrystallized from toluene

Quellen und Nachweise

ORD-Eintrag
ord-06ef5586f5e34257bbb312625d34d150
Quelldatensatz
uspto-grants-1993_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05264458

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