Diethyl Ether → 1-(Aminooxy)-3,3-dimethylbutan-2-ol

HRID 494739Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 494739
[OH:1][CH:2]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:3][O:4][N:5]1C(=O)C2C(=CC=CC=2)C1=O.CNN.C(OCC)C>ClCCl>[NH2:5][O:4][CH2:3][CH:2]([OH:1])[C:16]([CH3:19])([CH3:18])[CH3:17]

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 6061MethylhydrazineHCID 211115332-(2-Hydroxy-3,3-dimethylbutoxy)-isoindole-1,3-dione

Produkt 1

HCID 211115321-(Aminooxy)-3,3-dimethylbutan-2-olAusbeute 86,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(2-hydroxy-3,3-dimethylbutoxy)-isoindole-1,3-dione (1.47 g, 5.60 mmol) in dichloromethane (20 mL) cooled to 0° C. was added methylhydrazine (0.31 mL, 5.90 mmol). The white suspension was allowed to stir for 16 hours at room temperature. Diethyl ether (50 mL) was added and the solids were removed by filtration. The filtrate was concentrated, diluted with diethyl ether and the solids were removed by filtration. This procedure was repeated twice more and the final filtrate was concentrated to provide the desired product as a yellow liquid (0.643 g, 86%). 1H NMR (400 MHz, CDCl3) δ 4.87 (br s, 2H), 3.85 (q, 1H), 3.58 (q, 2H), 0.93 (s, 9H).

Aufarbeitung

  1. customthe solids were removed by filtration
  2. concentrationThe filtrate was concentrated
  3. additiondiluted with diethyl ether
  4. customthe solids were removed by filtration
  5. concentrationthe final filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-2ca3e4f120a2409a8e8d1a205e5f52a7
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538120B2

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