Triethylamine → 4-(4-Dimethylaminophenylsulfanyl)-2-methylpent-2-enoic acid methyl ester

HRID 2245775Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:10])[C:4]([CH3:9])=[CH:5][CH:6](Br)[CH3:7].C(N(CC)CC)C.[CH3:18][N:19]([CH3:27])[C:20]1[CH:25]=[CH:24][C:23]([SH:26])=[CH:22][CH:21]=1>C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:10])[C:4]([CH3:9])=[CH:5][CH:6]([S:26][C:23]1[CH:24]=[CH:25][C:20]([N:19]([CH3:27])[CH3:18])=[CH:21][CH:22]=1)[CH3:7]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 4-bromo-2-methylpent-2-enoic acid methyl ester (0.414 g, 2.0 mmol) in dry benzene (4 mL) under an atmosphere of argon was added a solution of triethylamine (0.28 mL, 2.0 mmol) and 4-dimethylamino-benzenethiol (0.306 g, 2.0 mmol) in dry benzene (2 mL). The mixture was stirred at 20° C. for 2 hours (TLC monitoring). The solvent was then removed under reduced pressure to give a yellow oil that was purified by column chromatography (20:79:1 diethyl ether:60-80° C. petroleum ether:triethylamine) to give the title compound (0.53 g, 95%) as a colourless oil.

Workup

customThe solvent was then removed under reduced pressure
customto give a yellow oil that
customwas purified by column chromatography (20:79:1 diethyl ether:60-80° C. petroleum ether:triethylamine)

Sources & evidence

ORD record: ord-14c09d9a8f2f47d2a8fe8ea808519453
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07683185B2

Reaction notes

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