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

HRID 858917Notes

Reaction equation

HRID 858917 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]([CH:24]=[CH:25]C(Cl)=O)([F:23])[F:22].[O:29]1CCC[CH2:30]1>>[F:23][C:21]([F:20])([F:22])[C:24](=[CH2:25])[C:30]([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:29]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 1365452-Methyl-2-adamantanolHCID 53780258Trifluoromethylacryloyl chloride

Product 1

HCID 113006922-(2-Trifluoromethyl-2-propenoyloxy)-2-methyladamantaneYield 70.3%

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

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

Sources & evidence

ORD record
ord-548f129a7a624154b2dec694914e473c
Source dataset
uspto-grants-2006_12
Patent number
US07148363B2

Reaction notes

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