反応式
[OH:1]C1C=CC=CC=1C(O)=O.C(OO)(C)(C)C.[CH3:17][CH:18]([C:20](=[CH:23][CH:24]=[C:25]([CH3:37])[CH2:26][CH2:27][CH:28]=[C:29]([CH3:36])[CH2:30][CH2:31][CH:32]=[C:33]([CH3:35])[CH3:34])[C:21]#[N:22])[CH3:19]>C(Cl)Cl.[Se](=O)=O>[OH:1][CH2:34][C:33]([CH3:35])=[CH:32][CH2:31][CH2:30][C:29]([CH3:36])=[CH:28][CH2:27][CH2:26][C:25]([CH3:37])=[CH:24][CH:23]=[C:20]([CH:18]([CH3:17])[CH3:19])[C:21]#[N:22]参加物
反応物 3
生成物 1
試薬・触媒・溶媒 2
実験手順
To a suspension of selenium dioxide (58 mg) and 2-hydroxybenzoic acid (365 mg) in methylene chloride (10.5 ml) was gradually added an aqueous solution of 80% t-butyl hydroperoxide (11.6 ml) with stirring on a water bath. After 30 minutes, 2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile (7.56 g, 26.8 mmol) was added to the mixture, which was then allowed to stand at room temperature for 30 hours. Most of the solvent was removed by evaporation in vacuo, and the residue was dissolved in ether. The organic layer was washed with saturated aqueous sodium bicarbonate, dried over MgSO4, and concentrated. The resultant residue was subjected to silica gel column chromatography to give the aimed 14-hydroxy-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile (2.53 g, 31%). The starting material was also recovered (3.10 g, 40%) in the column chromatography. The yield of the aimed product based on the consumed starting material was 52%.
後処理
- waitto stand at room temperature for 30 hours
- customMost of the solvent was removed by evaporation in vacuo
- dissolutionthe residue was dissolved in ether
- washThe organic layer was washed with saturated aqueous sodium bicarbonate
- dry with materialdried over MgSO4
- concentrationconcentrated
出典と根拠
- ORDレコード
- ord-c0dc6df34efc4c77bcfc23a67369e20a
- 出典データセット
- uspto-grants-1994_10
- 特許番号
- US05354874
関連ノート
読み込み中…