Ammonium Acetate → 3-[2-(4-Dibutylamino-2-methoxyphenyl)vinyl]-2-butyl-5,5-dimethyl-2-cyclohexenone

HRID 85338

Reaction equation

[Na].[CH2:2]([N:6]([CH2:17][CH2:18][CH2:19][CH3:20])[C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[C:9]([O:15][CH3:16])[CH:8]=1)[CH2:3][CH2:4][CH3:5].[CH2:21]([C:25]1[C:26](=[O:34])[CH2:27][C:28]([CH3:33])([CH3:32])[CH2:29][C:30]=1[CH3:31])[CH2:22][CH2:23][CH3:24].C([O-])(=O)C.[NH4+]>C(O)C.C(OCC)(=O)C>[CH2:2]([N:6]([CH2:17][CH2:18][CH2:19][CH3:20])[C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[CH:31][C:30]2[CH2:29][C:28]([CH3:32])([CH3:33])[CH2:27][C:26](=[O:34])[C:25]=2[CH2:21][CH2:22][CH2:23][CH3:24])=[C:9]([O:15][CH3:16])[CH:8]=1)[CH2:3][CH2:4][CH3:5]

Participants

Conditions

Temperature: 60 °C

Procedure

0.3 g (13.0 mmol) of sodium was dissolved in 15 ml of ethanol. Next, 2.63 g (10.0 mmol) of 4-dibutylamino-2-methoxybenzaldehyde and 2.22 g (11.0 mmol) of 2-butyl-3,5,5-trimethyl-2-cyclohexenone were dissolved in 5 ml of ethanol and added to the mixture. To this mixture, 0.36 g of ammonium acetate was added and the mixture was stirred with heating at 60° C. for 22 hours. To the mixture, 100 ml of ethyl acetate was added. Washing with a saturated saline solution, drying over anhydrous sodium sulfate, and concentration were performed. The residual liquid was purified by silica gel column chromatography to give 465 mg of a dark red oily matter (yield: 10.6%).

Workup

additionadded to the mixture
washWashing with a saturated saline solution
dry with materialdrying over anhydrous sodium sulfate, and concentration
customThe residual liquid was purified by silica gel column chromatography
customto give 465 mg of a dark red oily matter (yield: 10.6%)

Sources & evidence

ORD record: ord-3c4daaf907ac4998a292cf2de3c55ec4
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846955B2

Linked notes

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