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

HRID 1707772Notes

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 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-(2-tetrahydropyranyl)oxy-5,9-undecadien-2-one (70%). IR(film)cm-1 ; 2950, 2880, 1720, 1442, 1358, 1120, 1078, 1024, 905, 870, 815.

Workup

temperatureto cool to room temperature
extractionThe product was extracted with ether (20 mlx2)
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-9e1507b0d549441994cf0498b59ef91b
Source dataset: uspto-grants-1994_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05354874

Reaction notes

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