Tetrahydrofuran → 3-Phenylpropyl 4-ethyl phenyl ether

Reaktionsgleichung

[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]

Komponenten

Edukt 3

HCID 8028Tetrahydrofuran

HCID 312424-Ethylphenol

HCID 62714Lithium hydride

Produkt 1

HCID 606443123-Phenylpropyl 4-ethyl phenyl etherAusbeute 93 %

Versuchsvorschrift

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.