Tetrahydrofuran → (R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde oxime

HRID 1523675Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1523675
[CH3:1][C:2]1([CH3:10])[O:6][C@H:5]([C:7](=O)C)[CH2:4][O:3]1.C1COCC1.Cl.[NH2:17][OH:18].C([O-])([O-])=O.[Na+].[Na+]>O>[CH3:1][C:2]1([CH3:10])[O:6][C@H:5]([CH:7]=[N:17][OH:18])[CH2:4][O:3]1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 188603Ethanone, 1-(2,2-dimethyl-1,3-dioxolan-4-yl)-, (S)-HCID 443297Hydroxyamine hydrochloride

Produkt 1

HCID 86644159(R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde oximeAusbeute 97,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of (S)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanone (10.5 g, 72.8 mmol) in 150 (mL) THF: 60 mL water was added hydroxylamine hydrochloride (5.06 g, 72.8 mmol), and the reaction was stirred for 20 minutes. Na2CO3 (3.78 g, 35.7 mmol) was added and the reaction was stirred overnight. The reaction was extracted with ethyl acetate, washed with water and brine, dried over MgSO4, filtered and concentrated to afford (R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde oxime (10.3 g, 71.0 mmol, 97.4% yield).

Aufarbeitung

  1. stirringthe reaction was stirred overnight
  2. extractionThe reaction was extracted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-80c9ee5369684c37a652b38abd63c5c1
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079890B2

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