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

HRID 858917노트

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HRID 858917 반응식
[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]

참가 물질

5

반응물 4

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

생성물 1

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

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온도
0 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-548f129a7a624154b2dec694914e473c
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07148363B2

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