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

HRID 232554Notes

Reaction equation

HRID 232554 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

HCID 867501198-t-Butyl-1-oxaspiro(4,5)decane-3-one oximeYield 99.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-856286c2b09c4fef89daa4f589af7cc1
Source dataset
uspto-grants-1997_01
Patent number
US05591741

Reaction notes

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