Tetrahydrofuran → 3-Phenylpropyl 4-ethyl phenyl ether

HRID 71017

Reaction equation

HRID 71017 reaction equation
[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]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 312424-EthylphenolHCID 62714Lithium hydride

Product 1

HCID 606443123-Phenylpropyl 4-ethyl phenyl etherYield 93%

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a3bf17f6f09d407baeb08418925747ef
Source dataset
uspto-grants-2014_09
Patent number
US08822707B2

Linked notes

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