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

HRID 1707773Notes

Reaction equation

[C:1]([CH:4]([CH2:9][CH:10]=[C:11]([CH3:22])[CH2:12][CH2:13][CH:14]=[C:15]([CH3:21])[CH2:16][O:17][CH2:18][O:19][CH3:20])C(OC)=O)(=[O:3])[CH3:2].[Cl-].[Na+].O>CS(C)=O>[CH3:22][C:11]([CH2:12][CH2:13][CH:14]=[C:15]([CH3:21])[CH2:16][O:17][CH2:18][O:19][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-5,9-dimethyl-10-(methoxymethyl)oxy-4,8-decadienate (420 mg, 1.37 mmol) in methylsulfoxide (4 ml) were added sodium chloride (160 mg, 2.74 mmol) and water (0.1 ml), and the mixture was stirred at 150° C. After five hours, the reaction mixture was allowed to cool to room temperature, and water (10 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-(methoxymethyl)oxy- 5,9-undecadien-2-one (358 mg, 67%).

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-2e54efa61743498e9a93cd4442a20607
Source dataset: uspto-grants-1994_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05354874

Reaction notes

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