Triethylamine → 2-(2-Trifluoromethyl-2-propenoyloxy)-2-methyladamantane

HRID 2308030Notes

Reaction equation

[CH3:1][C:2]1([OH:12])[CH:9]2[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.C(N(CC)CC)C.[F:20][C:21]([F:28])([F:27])[C:22](=[CH2:26])[C:23](Cl)=[O:24]>O1CCCC1>[F:20][C:21]([F:28])([F:27])[C:22](=[CH2:26])[C:23]([O:12][C:2]1([CH3:1])[CH:3]2[CH2:11][CH:7]3[CH2:6][CH:5]([CH2:10][CH:9]1[CH2:8]3)[CH2:4]2)=[O:24]

Participants

Conditions

Temperature: 0 °C

Procedure

A 500 ml flask was flushed with nitrogen to displace the air with nitrogen, and was charged with 83.1 g (0.50 mol) of 2-methyl-2-adamantanol, 101.2 g (1.0 mol) of triethylamine and 200 g of tetrahydrofuran. Then 118.9 g (0.75 mol) of α-trifluoromethylacryloyl chloride was dropwise added to the content in the flask over a period of about 1 hour, while the content was maintained at a reaction temperature of about 0° C. Then the content was stirred for 10 hours at room temperature. After completion of the reaction, the reaction mixture was washed with water and then with an aqueous saturated sodium chloride solution. The thus-obtained organic phase was subjected to column chromatography, and further, analyzed by NMR and mass spectrometry. Thus, 101.2 g (yield: 70.3%) of the object 2-methyl-2-adamantyl α-trifluoromethylacrylate was obtained.

Workup

customA 500 ml flask was flushed with nitrogen
customAfter completion of the reaction
washthe reaction mixture was washed with water

Sources & evidence

ORD record: ord-037f258cd14b4049990a9998f3b38c3f
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06833462B2

Reaction notes

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