Tetrahydrofuran → 3-Phenylpropyl 4-ethyl phenyl ether

HRID 71017

반응식

HRID 71017 반응식
[H-].[Li+].[CH2:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[CH3:4].[CH2:12]1[CH2:16]O[CH2:14][CH2:13]1>>[CH2:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:14][CH2:13][CH2:12][C:16]2[CH:7]=[CH:6][CH:5]=[CH:3][CH:4]=2)=[CH:7][CH:6]=1)[CH3:4]

참가 물질

4

반응물 3

HCID 8028TetrahydrofuranHCID 312424-EthylphenolHCID 62714Lithium hydride

생성물 1

HCID 606443123-Phenylpropyl 4-ethyl phenyl ether수율 93%

실험 절차

To a suspension of LiH (0.005 g, 0.6 mmol) in THF was added p-ethyl phenol (0.08 g, 0.68 mmol) very slowly at 0° C. After 30 min of stirring at room temperature, the sulfonate ester, 2a (0.075 g, 0.17 mmol) was added to it and the reaction mixture was heated at 65° C. for 8 h. The reaction mixture was washed very carefully with cold water and extracted in EtOAc and dried over sodium sulfate. The organic layer was evaporated and the crude gummy material was purified by flash chromatography giving 0.038 g (93%) of an oil. 1H NMR (400 MHz, CDCl3) δ 7.31-7.18 (m, 5H), 7.13-7.09 (m, 2H), 6.85-6.81 (m, 2H), 3.94 (t, J=6.2 Hz, 2H), 2.84 (t, J=7.6 Hz, 2H), 2.58 (q, J=7.5, 2H), 2.13-2.03 (m, 2H), 1.21 (t, J=7.5 Hz, 3H); 13CNMR (100.75 MHz, CDCl3) 141.8, 130.6, 128.9, 128.7, 128.6, 126.1, 114.6, 67.1, 32.4, 31.1, 28.2, 16.1; HRMS (EI) [M]+: calcd for C17H20O 240.1514, found 240.1510.

후처리

  1. temperaturethe reaction mixture was heated at 65° C. for 8 h
  2. washThe reaction mixture was washed very carefully with cold water
  3. extractionextracted in EtOAc
  4. dry with materialdried over sodium sulfate
  5. customThe organic layer was evaporated
  6. customthe crude gummy material was purified by flash chromatography

출처 및 근거

ORD 기록
ord-a3bf17f6f09d407baeb08418925747ef
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822707B2

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