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Allyl bromide → HCID 12083067, Verbindung

HRID 1168846
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1168846
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][N:3]=1.[CH2:11](Br)[CH:12]=[CH2:13].[Li+].CC([N-]C(C)C)C.C(OCC)(=O)C>C1COCC1.O>[CH2:1]([C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][N:3]=1)[CH2:13][CH:12]=[CH2:11]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 7841Allyl bromideHCID 8857Ethyl AcetateHCID 2724682Lithium diisopropylamideHCID 40681043-Methylbenzo[d]isoxazole

Produkt 1

HCID 12083067HCID 12083067, VerbindungAusbeute 103,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3.0 mL dry THF was added to an oven-dried 25 mL flask and cooled to −78° C. on a dry ice/isopropanol bath. Diisopropylamine (840 μl, 6.0 mmol) was added followed by n-BuLi (3.8 mL, 1.6 M, 6.0 mmol). The LDA-solution that was obtained was left at room temperature. Compound 25 (666 mg, 5.0 mmol) was dissolved in 10 mL dry THF and added to an oven-dried 50 mL flask followed by allylbromide (476 μl, 5.5 mmol). The freshly prepared LDA-solution was slowly added at −78° C. and the mixture was left at room temperature for 30 min. Ethyl acetate and water were added. The phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over magnesium sulphate and evaporated to dryness to produce 893 mg of a light brown oil. Crude product was purified by column chromatography (heptane:ethyl acetate; 9:1; isocratic) to produce pure 26 (355 mg, 41%).

Aufarbeitung

  1. waitwas left at room temperature
  2. additionadded to an oven-dried 50 mL flask
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate
  5. dry with materialThe combined organic phases were dried over magnesium sulphate
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-120218ca4bc14a2a870de20a1bca59a3
Quelldatensatz
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06627645B2

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