반응 #816886

반응 방정식

NEt3

4-iodotetrahydropyran

ethyl(4-mercaptophenyl)acetate

→

title compound

Ethyl[4-(tetrahydropyran-4-ylsulfanyl)phenyl]acetate

용매

DMF

반응 조건

후처리

1. 1
   기타the solvents were removed under reduced pressure
2. 2
   기타The residue was partitioned between Et2O (100 mL) and saturated aqueous NH4Cl (50 mL)
3. 3
   추출the aqueous phase being extracted further with Et2O (45 mL)
4. 4
   세척The combined ethereal extracts were washed with H2O (50 mL), H2O-saturated aqueous Na2CO3 (1:1, 50 mL), and brine (50 mL)
5. 5
   건조before being dried (MgSO4)
6. 6
   여과Filtration, solvent evaporation, and flash chromatography (IH-Et2O, 10:1 to 2:1)

실험 절차

NEt3 (1.3 mL, 9.0 mmol) and 4-iodotetrahydropyran (1.93 g, 9.0 mmol) were added to a stirred solution of ethyl(4-mercaptophenyl)acetate (1.21 g, 6.0 mmol) in anhydrous DMF (10 mL) at 0° C. The mixture was allowed to warm to room temperature over 3 d, then the solvents were removed under reduced pressure. The residue was partitioned between Et2O (100 mL) and saturated aqueous NH4Cl (50 mL), the aqueous phase being extracted further with Et2O (45 mL). The combined ethereal extracts were washed with H2O (50 mL), H2O-saturated aqueous Na2CO3 (1:1, 50 mL), and brine (50 mL), before being dried (MgSO4). Filtration, solvent evaporation, and flash chromatography (IH-Et2O, 10:1 to 2:1) afforded the title compound: RF (IH-Et2O, 2:1)=0.31.

출처