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

HRID 1110167Notes

Reaction equation

[C:1]([CH:4]([CH2:9][CH:10]=[C:11]([CH3:25])[CH2:12][CH2:13][CH:14]=[C:15]([CH3:24])[CH2:16][O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1)C(OC)=O)(=[O:3])[CH3:2].[Cl-].[Na+].O>CS(C)=O>[CH3:25][C:11]([CH2:12][CH2:13][CH:14]=[C:15]([CH3:24])[CH2:16][O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1)=[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-5,9-dimethyl-10-(2-tetrahydropyranyl)oxy-4,8-decadienate (370 mg, 1.05 mmol) in methylsulfoxide (2 ml) were added sodium chloride (180 mg, 3.08 mmol) and water (0.1 ml), and the mixture was stirred at 150° C. After four hours, the reaction mixture was allowed to cool to room temperature, and water (15 ml) was added thereto. The product was extracted with ether (20 ml×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-(2-tetrahydropyranyl)oxy-5,9-undecadien-2-one (70%).

Workup

temperatureto cool to room temperature
extractionThe product was extracted with ether (20 ml×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-a330e7f92d67455785bf6bb9d1e0766d
Source dataset: uspto-grants-1994_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05324869

Reaction notes

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