Tetrahydrofuran → 3-Phenylpropyl 4-ethyl phenyl ether

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

반응물 3

HCID 8028Tetrahydrofuran

HCID 312424-Ethylphenol

HCID 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.