Water → 6,10-Dimethyl-11-(dimethyl t-butylsilyl)oxy-5,9-undecadien-2-one

HRID 1707774ノート

反応式

HRID 1707774 の反応式
[C:1]([CH:4]([CH2:9][CH:10]=[C:11]([CH3:26])[CH2:12][CH2:13][CH:14]=[C:15]([CH3:25])[CH2:16][O:17][Si:18]([CH3:24])([CH3:23])[C:19]([CH3:22])([CH3:21])[CH3:20])C(OC)=O)(=[O:3])[CH3:2].[I-].[Na+].O>CN(C)P(=O)(N(C)C)N(C)C>[CH3:26][C:11]([CH2:12][CH2:13][CH:14]=[C:15]([CH3:25])[CH2:16][O:17][Si:18]([CH3:24])([CH3:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:10][CH2:9][CH2:4][C:1](=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 962Water2 回HCID 5238Sodium IodideHCID 54555482Methyl 2-acetyl-10-(dimethyl t-butylsilyl)oxy-5,9-dimethyl-4,8-decadienate

生成物 1

HCID 540598486,10-Dimethyl-11-(dimethyl t-butylsilyl)oxy-5,9-undecadien-2-one収率 70.2%

試薬・触媒・溶媒 1

HCID 12679Hexamethylphosphoramide溶媒

反応条件

温度
150 °C

実験手順

To a solution of methyl 2-acetyl-10-(dimethyl t-butylsilyl)oxy-5,9-dimethyl-4,8-decadienate (96 mg, 0.25 mmol) in hexamethylphosphoric triamide (0.5 ml) were added sodium iodide (45 mg, 0.30 mmol) and water (0.01 ml), and the mixture was stirred at 150° C. After two hours, the reaction mixture was allowed to cool to room temperature, and water (2 ml) was added thereto. The product was extracted with ether (5 mlx2). The extract was dried over Na2SO4, and concentrated to give a residue, which was then purified with silica gel column chromatography to obtain 6,10-dimethyl-11-(dimethyl t-butylsilyl)oxy-5,9-undecadien-2-one (57 mg, 70%).

後処理

  1. temperatureto cool to room temperature
  2. extractionThe product was extracted with ether (5 mlx2)
  3. dry with materialThe extract was dried over Na2SO4
  4. concentrationconcentrated
  5. customto give a residue, which
  6. customwas then purified with silica gel column chromatography

出典と根拠

ORDレコード
ord-d9be36632fa2477b81ebde35ae204e7e
出典データセット
uspto-grants-1994_10
特許番号
US05354874

反応ノート

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