2-(Dimethylamino)ethanol → 6-(2-Dimethylaminoethoxy)-1-tetralone

HRID 32108

Reaktionsgleichung

Reaktionsgleichung von HRID 32108
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2

Komponenten

6

Edukt 4

HCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Produkt 1

HCID 122143876-(2-Dimethylaminoethoxy)-1-tetralone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 6-hydroxy-1-tetralone (Aldrich, 1.0 g, 6.17 mmol, 1.0 eq), N,N-dimethylethanolamine (Aldrich, 0.93 mL, 9.26 mmol, 1.5 eq), and triphenylphosphine (Aldrich, 2.43 g, 9.26 mmol, 1.5 eq) in THF (10 mL) was added diethyl azodicarboxylate (Aldrich, 1.94 mL, 12.34 mmol, 2.0 eq) at 0° C. The reaction mixture was gradually warmed to RT and continued to stir overnight. The solvent was evaporated in vacuo. The residue was purified by silica gel chromatography (3%-5% MeOH—CH2Cl2) to provide the product as orange oil. MS (ESI): 234 (M+H)+.

Aufarbeitung

  1. customThe solvent was evaporated in vacuo
  2. customThe residue was purified by silica gel chromatography (3%-5% MeOH—CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-30652c6c4f424175b90fd002eef49a3c
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425631B2

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