反应详情

DMSO (118 mL, 1.6674 mol) was added dropwise to a solution of 126.42 g (0.579 mol) of 1-cyclohexyl-2-phenylpropanol in 1737 mL of CH2Cl2 (cooled in a wet ice acetone bath). After 29 min, 147.93 g (1.0422 mol) of P2O5 was added. After 11 min, the cooling bath was removed. An aliquot quenched with Et3N showed complete reaction within 3 h at RT. The reaction mixture was cooled in a wet ice acetone bath. Et3N (282 mL, 2.0265 mol) was added dropwise to the cooled reaction mixture over a 30 min period. The cooling bath was removed and the mixture was stirred overnight at RT. The reaction mixture was quenched by dropwise addition of 500 mL of 3 N HCl (aq) (pH=0). After shaking in separatory funnel, the aqueous phase was removed. The organic phase was washed with 500 mL of 3 N HCl (aq) (pH=0), washed twice with 1 L of 10% K2CO3 (aq) (pH=12;12), washed three times with 500 mL of NaOCl (aq) solution, washed with 1L of water, washed with 1 L of 25% NaCl (aq), dried over MgSO4, gravity filtered and concentrated under vacuum with dry ice trap to collect Me2S. An amber oil of the title compound (107.01 g, 85.437%) was obtained;

1. waitAfter 11 min
2. customthe cooling bath was removed
3. customAn aliquot quenched with Et3N showed complete reaction within 3 h at RT
4. temperatureThe reaction mixture was cooled in a wet ice acetone bath
5. customThe cooling bath was removed
6. customThe reaction mixture was quenched by dropwise addition of 500 mL of 3 N HCl (aq) (pH=0)
7. stirringAfter shaking in separatory funnel
8. customthe aqueous phase was removed
9. washThe organic phase was washed with 500 mL of 3 N HCl (aq) (pH=0)
10. washwashed twice with 1 L of 10% K2CO3 (aq) (pH=12;12)
11. washwashed three times with 500 mL of NaOCl (aq) solution
12. washwashed with 1L of water
13. washwashed with 1 L of 25% NaCl (aq)
14. dry with materialdried over MgSO4, gravity
15. filtrationfiltered
16. concentrationconcentrated under vacuum with dry ice trap
17. customto collect Me2S