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

HRID 858917ノート

反応式

HRID 858917 の反応式
[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]

参加物

5

反応物 4

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

生成物 1

HCID 113006922-(2-Trifluoromethyl-2-propenoyloxy)-2-methyladamantane収率 70.3%

反応条件

温度
0 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-548f129a7a624154b2dec694914e473c
出典データセット
uspto-grants-2006_12
特許番号
US07148363B2

反応ノート

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