Reaction #816886

Reaction equation

NEt3

4-iodotetrahydropyran

ethyl(4-mercaptophenyl)acetate

→

title compound

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

Solvents

DMF

Conditions

Workup

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

Procedure

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.

Source