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

HRID 1707774노트

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HRID 1707774 반응식
[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]

참가 물질

5

반응물 3

HCID 962Water2회HCID 5238Sodium IodideHCID 54555482Methyl 2-acetyl-10-(dimethyl t-butylsilyl)oxy-5,9-dimethyl-4,8-decadienate

생성물 1

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

시약·촉매·용매 1

HCID 12679Hexamethylphosphoramide용매

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온도
150 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-d9be36632fa2477b81ebde35ae204e7e
출처 데이터셋
uspto-grants-1994_10
특허 번호
US05354874

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