反应详情

A solution of 2-(3,3-diphenyl-1-propyloxy)ethanol (2.5 g, 0.010 mol) in dry THF (20 ml) was placed on an ice-bath and a solution of n-butyllithium in hexanes (4.0 ml, 2.5 M) was added dropwise under an atmosphere of nitrogen. When addition was complete the reaction mixture was stirred at room temperature for 0.5 h and then heated at reflux temperature for 1 h. The mixture was cooled to room temperature and p-toluenesulphonyl chloride (2.1 g, 0.011 mol) was added. The mixture was stirred at room temperature for 0.5 h and then heated at reflux temperature for 1 h. To the cooled reaction mixture was added dry potassium carbonate (2.0 g, 0.015 mol) and ethyl (R)-3-piperidinecarboxylate (2.0 g, 0.0125 mol) and the mixture was heated at reflux temperature for 3 h. The cooled reaction mixture was poured into water (200 ml) and extracted with ethyl acetate (2×200 ml). The combined organic extracts was dried over sodium sulphate and the solvent evaporated in vacuo. The residue was submitted to flash chromatography on silica gel (150 g) using a mixture of n-heptane and THF (4:1) as eluent. This provided 0.9 g (11% calculated from 3,3-diphenyl-1-propanol) of the title compound as an oil. TLC: rf=0.24 (SiO2 ; n-heptane/THF=7:3). 1H NMR δ (CDCl3) 4.10 (t, 1H).

1. additionWhen addition
2. temperatureheated
3. temperatureat reflux temperature for 1 h
4. temperatureThe mixture was cooled to room temperature
5. stirringThe mixture was stirred at room temperature for 0.5 h
6. temperatureheated
7. temperatureat reflux temperature for 1 h
8. customTo the cooled reaction mixture
9. temperaturethe mixture was heated
10. temperatureat reflux temperature for 3 h
11. customThe cooled reaction mixture
12. extractionextracted with ethyl acetate (2×200 ml)
13. dry with materialThe combined organic extracts was dried over sodium sulphate
14. customthe solvent evaporated in vacuo
15. additiona mixture of n-heptane and THF (4:1) as eluent