Triethylamine → Dimethyl 4-{2-[5-(2-ethyl-[1,3]dioxolan-2-yl)-2-thienyl]ethyl}phthalate

HRID 49336Notes

Reaction equation

[CH2:1]([C:3]1([C:8]2[S:12][C:11](/[CH:13]=[CH:14]/[C:15]3[CH:16]=[C:17]([C:25]([O:27][CH3:28])=[O:26])[C:18](=[CH:23][CH:24]=3)[C:19]([O:21][CH3:22])=[O:20])=[CH:10][CH:9]=2)[O:7][CH2:6][CH2:5][O:4]1)[CH3:2].C(N(CC)CC)C>O1CCOCC1>[CH2:1]([C:3]1([C:8]2[S:12][C:11]([CH2:13][CH2:14][C:15]3[CH:16]=[C:17]([C:25]([O:27][CH3:28])=[O:26])[C:18](=[CH:23][CH:24]=3)[C:19]([O:21][CH3:22])=[O:20])=[CH:10][CH:9]=2)[O:7][CH2:6][CH2:5][O:4]1)[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

9.3 g (23 mmol) of dimethyl 4-{(E)-2-[5-(2-ethyl-[1,3]dioxolan-2-yl)-2-thienyl]vinyl}phthalate are dissolved in 150 mL of dioxane and 1 mL of triethylamine is then added. The mixture is degassed using a stream of nitrogen and 9.3 g of 5% palladium-on-charcoal are then added to the reaction medium. A positive pressure of hydrogen is maintained in the reaction medium for 5 hours, with heating at 80° C. After cooling and then filtration through Celite and evaporation, the desired product is obtained in the form of a yellow oil (m=9.4 g; Y=100%).

Workup

customThe mixture is degassed
additionare then added to the reaction medium
temperatureA positive pressure of hydrogen is maintained in the reaction medium for 5 hours
temperatureAfter cooling
filtrationfiltration
customthrough Celite and evaporation

Sources & evidence

ORD record: ord-c38a697ede9a4017b06ab90de20e18a3
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706725B1

Reaction notes

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