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

HRID 1684689ノート

反応式

HRID 1684689 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-092832722e8f4400b3ec1212a330ac78
出典データセット
uspto-grants-1997_06
特許番号
US05641883

反応ノート

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