Triethylamine → 8-t-Butyl-1-oxaspiro(4,5)decane-3-one oxime

HRID 232554Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 232554
Cl.[NH2:2][OH:3].C(N(CC)CC)C.[C:11]([CH:15]1[CH2:25][CH2:24][C:18]2([O:22][CH2:21][C:20](=O)[CH2:19]2)[CH2:17][CH2:16]1)([CH3:14])([CH3:13])[CH3:12]>O.O1CCCC1>[C:11]([CH:15]1[CH2:25][CH2:24][C:18]2([O:22][CH2:21][C:20](=[N:2][OH:3])[CH2:19]2)[CH2:17][CH2:16]1)([CH3:14])([CH3:13])[CH3:12]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 151828188-t-Butyl-1-oxaspiro(4,5)decane-3-one

Produkt 1

HCID 867501198-t-Butyl-1-oxaspiro(4,5)decane-3-one oximeAusbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of hydroxylamine hydrochloride (6.9 g, 0.1 mol) and triethylamine (10.0 g, 0.1 mol) in 10 ml of water was added 8-t-butyl-1-oxaspiro(4,5)decane-3-one (16.0 g, 0.076 mol) in 30 ml tetrahydrofuran. The mixture was stirred at room temperature for 3 hours and at 60° C. for 1 hour. The solvent was then evaporated in vacuo and the residue was partitioned between toluene and brine (100 ml each). The organic layer was washed with brine, dried (MgSO4) and evaporated in vacuo to yield a colourless oil (17.0 g) which crystallised on standing. Recrystallisation from light petroleum gave two fractions of colourless crystals (6.6 g and 5.3 g) mp.: 118°-120 and 105-108° C. 1H-NMR indicated mixtures of geometric isomers (E/Z) in ratios of 1:1 and 2:1 respectively.

Aufarbeitung

  1. customThe solvent was then evaporated in vacuo
  2. customthe residue was partitioned between toluene and brine (100 ml each)
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-856286c2b09c4fef89daa4f589af7cc1
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05591741

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