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Diethyl Ether → 1-(2-Benzyloxyethyl)-4-methyl-2,6,7-trioxabicyclo-[2.2.2]octane

HRID 1250274
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1250274
[CH2:1]([O:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][C:15]1([CH3:19])[CH2:18][O:17][CH2:16]1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FB(F)F.C(OCC)C.C(N(CC)CC)C.C(OCC)C>ClCCl>[CH2:1]([O:8][CH2:9][CH2:10][C:11]12[O:12][CH2:16][C:15]([CH3:19])([CH2:14][O:13]1)[CH2:18][O:17]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 8000Boron trifluoride etherateHCID 8471TriethylamineHCID 541789563-Methyl-3-oxetanylmethyl 3-benzyloxypropionate

Produkt 1

HCID 183273631-(2-Benzyloxyethyl)-4-methyl-2,6,7-trioxabicyclo-[2.2.2]octaneAusbeute 73,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

3-Methyl-3-oxetanylmethyl 3-benzyloxypropionate (521 mg) was dissolved in dichloromethane under an argon atmosphere, and trifluoroborane-diethylether was added thereto at −15° C. The mixture was stirred for 5 hours at −15° C. Triethylamine (280 μl) was added to the reaction mixture, and stirring was continued for 15 minutes. Subsequently, diethylether (3 ml) was added. The precipitating crystals were removed from the reaction mixture by filtration, then the mother liquid was concentrated under reduced pressure. The residue was purified by alumina column chromatography (ethyl acetate-hexane 1:3), to give 385 mg of 1-(2-benzyloxyethyl)-4-methyl-2,6,7-trioxabicyclo-[2.2.2]octane as a colorless solid.

Aufarbeitung

  1. customat −15° C
  2. stirringstirring
  3. waitwas continued for 15 minutes
  4. customThe precipitating crystals were removed from the reaction mixture by filtration
  5. concentrationthe mother liquid was concentrated under reduced pressure
  6. customThe residue was purified by alumina column chromatography (ethyl acetate-hexane 1:3)

Quellen und Nachweise

ORD-Eintrag
ord-8e0f52b290c149be9b98bd030643b5fc
Quelldatensatz
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06337334B1

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