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Aluminium lithium hydride → (3-(8-(1,3-Dioxolan-2-yl)octyloxy)phenyl)(phenyl)methanamine

HRID 332649
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 332649
[N:1]([CH:4]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:5]1[CH:6]=[C:7]([CH:22]=[CH:23][CH:24]=1)[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]1[O:21][CH2:20][CH2:19][O:18]1)=[N+]=[N-].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[O:18]1[CH2:19][CH2:20][O:21][CH:17]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][C:7]1[CH:6]=[C:5]([CH:4]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[NH2:1])[CH:24]=[CH:23][CH:22]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 710931432-(8-(3-(Azido(phenyl)methyl)phenoxy)octyl)-1,3-dioxolane

Produkt 1

HCID 71093129(3-(8-(1,3-Dioxolan-2-yl)octyloxy)phenyl)(phenyl)methanamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 2-(8-(3-(azido(phenyl)methyl)phenoxy)octyl)-1,3-dioxolane (1.11 g, 2.71 mmol) in THF (15 mL) at −78° C. under an atmosphere of nitrogen, a solution of lithium aluminium hydride (2.0M in THF, 2.8 mL, 5.60 mmol) was added drop wise. After stirring the reaction at −78° C. for 1 hour, the reaction mixture was warmed up to 0° C. for 1 hour. The reaction mixture was quenched with water (304 mL), 2M sodium hydroxide (304 mL) and water (304 mL×3). Anhydrous magnesium sulphate and ethyl acetate were added, and the reaction mixture filtered and concentrated under reduced pressure. The crude material was purified by column chromatography eluting with 100% iso-hexane to 100% DCM to 25:1 DCM:methanol (0.63 g, 39% based on (3-(8-(1,3-dioxolan-2-yl)octyloxy)phenyl)(phenyl)methanol).

Aufarbeitung

  1. customthe reaction at −78° C. for 1 hour
  2. customThe reaction mixture was quenched with water (304 mL), 2M sodium hydroxide (304 mL) and water (304 mL×3)
  3. additionAnhydrous magnesium sulphate and ethyl acetate were added
  4. filtrationthe reaction mixture filtered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by column chromatography
  7. washeluting with 100% iso-hexane to 100% DCM to 25:1 DCM

Quellen und Nachweise

ORD-Eintrag
ord-b40ee59728714d03a3d5bb4c3c94ce3f
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08877774B2

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