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

HRID 5657

Reaction equation

[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]

Participants

Conditions

Temperature: 150 °C

Procedure

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 m1×2). 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%).

Workup

temperatureto cool to room temperature
extractionThe product was extracted with ether (5 m1×2)
dry with materialThe extract was dried over Na2SO4
concentrationconcentrated
customto give a residue, which
customwas then purified with silica gel column chromatography

Sources & evidence

ORD record: ord-df3ec79a7f2a4004a3d61a7c5b0fd4ee
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05245085

Linked notes

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