反应详情

温度

0 °C

To a mixture of ethyl 2-ethyl-4-hydroxycyclopentanecarboxylate (37.78 g, 203 mmol, Preparation #P.1) in DCM (100 mL) and cyclohexane (200 mL) at about 0° C. was added 4-methoxybenzyl 2,2,2-trichloroacetimidate (93.58 g, 331 mmol) followed by dropwise addition of trifluoromethanesulfonic acid (1.6 mL, 18.0 mmol) over about 35 min. The reaction mixture was stirred at about 0° C. for about 30 min. The ice bath was removed and the reaction mixture was stirred at ambient temperature for about 16 h. The suspension was poured into ice-water (500 mL) and stirred for about 30 min. The solid was removed by filtration while washing with DCM (100 mL). The layers in the filtrate were separated and the aqueous layer was extracted with DCM (3×200 mL). The combined organic layers were washed with water (200 mL), dried over anhydrous MgSO4, filtered, and concd under reduced pressure. The crude material was purified using silica gel chromatography eluting with a gradient of 0-100% DCM:EtOAc (95:5) in DCM to give ethyl 2-ethyl-4-(4-methoxybenzyloxy)cyclopentanecarboxylate (39.80 g, 64%): LC/MS (Table 1, Method b) Rt=2.90 min; MS m/z: 307 (M+H)+.

1. customThe ice bath was removed
2. stirringthe reaction mixture was stirred at ambient temperature for about 16 h
3. additionThe suspension was poured into ice-water (500 mL)
4. stirringstirred for about 30 min
5. customThe solid was removed by filtration
6. washwhile washing with DCM (100 mL)
7. customThe layers in the filtrate were separated
8. extractionthe aqueous layer was extracted with DCM (3×200 mL)
9. washThe combined organic layers were washed with water (200 mL)
10. dry with materialdried over anhydrous MgSO4
11. filtrationfiltered
12. customThe crude material was purified
13. washeluting with a gradient of 0-100% DCM:EtOAc (95:5) in DCM